November 12, 2025 Board of Supervisors Windward Community Development District Dear Board Members: The regular meeting of the Board of Supervisors of the Windward Community Development District will be held Wednesday, November 19, 2025 at 1:00 p.m. at 7813 Four Seasons Blvd., Kissimmee, Florida 34747. Following is the agenda for the meeting: Board of Supervisors Meeting 1. Call to Order 2. Roll Call 3. Pledge of Allegiance 4. Public Comment Period 5. Approval of Minutes of the October 15, 2025 Board of Supervisors Meeting 6. Consideration of Proposals A. Landscape Lighting at Front Gate with TPG Lighting B. Roundabout Planting on Four Seasons Blvd. with United Land Services C. Sod Replacement in Verge United Land Services D. Seal Coat Options- Bike Lane Markings Removal with Sealcoat Florida E. Security Estimates i. Infinite Security ii. Insyte Security 7. Approval of Engineering Request for Qualifications 8. Staff Reports A. Attorney B. Engineer C. District Manager i. Approval of Check Register ii. Paid/ Unpaid Invoices for Approval iii. Balance Sheet and Income Statement D. Field Manager 9. Other Business 10. Supervisors’ Requests 11. Adjournment MINUTES OF MEETING WINDWARD COMMUNITY DEVELOPMENT DISTRICT The regular meeting of the Board of Supervisors of the Windward Community Development District was held Wednesday, October 15, 2025 at 1:00 p.m. at 7813 Four Seasons Boulevard, Kissimmee, Florida. Present and constituting a quorum were: Tim Peltier Greg Bobonik Ernest Hofer Erik Rose Steve Pierson Also Present were: Jason Showe Kristen Trucco Steven Saha Jarett Wright FIRST ORDER OF BUSINESS Mr. Showe called the meeting to order. SECOND ORDER OF BUSINESS Mr. Showe called the roll. THIRD ORDER OF BUSINESS Chairman Vice Chairman Assistant Secretary Assistant Secretary Assistant Secretary District Manager District Counsel District Engineer Field Manager Call to Order Roll Call Pledge of Allegiance Mr. Showe led the pledge of allegiance. FOURTH ORDER OF BUSINESS Public Comment Ms. Williams stated the oak in front of my house in the verge pushed up the sidewalk, it had been marked, it looks like someone came through and did the sanding down, but it still has some edges that can trip someone. It’s the first house as you turn right on Estuary. That intersection coming from Four Seasons Boulevard onto Estuary people drive very fast and swing a little bit wide. There are two houses, the second and third houses park their cars on the street all the time and there have been a lot of near misses when people come around the corner so fast. I think we need to do something. Both houses have empty driveways but they park on the street in an area that is like that. When you are coming from Sabal Point Loop onto Estuary towards Four Seasons you cannot see the people coming down the street, you have to pull way out. I don’t know that signage would help but we need to do something because there is going to be an accident. If we have some money for landscaping the hedge on Four Seasons Boulevard, put in a couple plants to replace some of the dead plants and there is still a big hole. If you can get bigger plants so it can fill in sooner, I would appreciate it. What is with the gates always breaking? Mr. Hilton stated we put all these live oak trees in and they drop acorns. My wife slipped on those a couple of times. Who is liable is someone falls? Ms. Trucco stated we will look at it internally and review that. FIFTH ORDER OF BUSINESS Approval of the Minutes of the September 24, 2025 Meeting Mr. Showe presented the minutes of the September 24, 2025 meeting and asked for any comments, corrections, or changes. On MOTION by Mr. Bobonik seconded by Mr. Hofer with all in favor the minutes of the September 24, 2025 meeting were approved as amended. SIXTH ORDER OF BUSINESS Approval of Draft Landscape Services Agreement with United Land Services Mr. Showe presented the draft landscape services agreement with United Land Services. On MOTION by Mr. Peltier seconded by Mr. Bobonik with all in favor the landscape services agreement with United Land Services was approved. SEVENTH ORDER OF BUSINESS Staff Reports A. Attorney Ms. Trucco stated we spoke at the workshop about some of the pending items but there is nothing new to report today. I will continue to track and follow-up on the 558 notice that we sent out and also the demand letter to the prior landscape company. B. Engineer There being no comments, the next item followed. C. Manager i. Approval of Check Register On MOTION by Mr. Hofer seconded by Mr. Peltier with all in favor the check register was approved except for the Guardian invoice 253976 and United invoice 147341. ii. Paid/Unpaid Invoices for Approval iii. Balance Sheet and Income Statement A copy of the balance sheet and income statement were included in the agenda package. D. Field Manager Mr. Wright stated we are waiting on a few more proposals for sidewalk repair to come in and the recommendation right now is most likely to be to inject the sidewalks, that will give you a more sturdy base and easier to level everything than spending hours grinding. I recommend setting a not to exceed for $55,000. The current proposal is for $45,600 and $55,000 would give us wiggle room for anything else that would be potentially identified at this time. We want this number to be lower than our current proposal is but if we set a not to exceed and have a board member for final approval then we can get this going as soon as possible. On MOTION by Mr. Bobonik seconded by Mr. Rose with all in favor staff was authorized to contract for sidewalk repair in an amount not to exceed $55,000 and the chairman was delegated authority to execute the agreement. Mr. Wright stated with the roundabout proposals we are looking at changing to have a little better aesthetic improving everything. The United Land Proposal was slightly different than Prince’s and we have to go back to make it apples to apples comparison and we will bring this to the next meeting. Mr. Wright reviewed the field manager’s report, copy of which was included in the agenda package. Mr. Hofer stated when the sidewalk grinding starts you are not going to want to walk in that area. EIGHTH ORDER OF BUSINESS Additional Audience Comments A resident stated I heard the gentlemen who proposed to increase it to $55,000 for the sidewalks say that filling them would prevent having to grind them. Did I hear that correctly? Mr. Wright stated they come in and drill a few holes, put the foam in and it is a much quicker process, it lifts it up. It is a more long-term solution. It’s an alternative to grinding. A resident asked is that money already in the budget or will it be an additional expense. Mr. Showe stated I think there is sufficient funds in the budget to accomplish it. A resident asked are we going to tape off the areas you are going to be working on so people don’t fall or walk there? Ms. Trucco stated I’m sure the contractor will do something. A resident stated these oak trees are already causing havoc. Have we thought about trimming or removing them? Ms. Trucco stated the board has looked into that, that is part of our 558. Mr. Peltier stated as mentioned we have to be careful when we are out because the oak trees are dropping acorns and that is part of the 558 we area addressing with Khov. Everybody needs to be cautious when out walking. NINTH ORDER OF BUSINESS Supervisor’s Requests Mr. Bobonik stated the enhancements up front has already started. On the exit side where the golf cart path goes across, the bushes are going to be removed for safety. They jumped the gun and instead of cutting it even to match the entrance side, they cut it down and it is only 2-feet tall. Now when you drive out you see everything on the golf course, restroom facility, etc. I have a meeting tomorrow morning with them to figure out how to fix this quickly. Some of the things we are still working on is the fountains, both sides have now been converted to fountains and the sluices that are still left are waterfalls. We are still looking for alternatives to cover those. We are looking at enhancing the lighting upfront, the signage will be changed. We will start on the guardhouse on October 20th weather permitting and once the painting is finished we will install permanent lighting. Once the monuments are fixed they will also get permanent lighting. We will replace the halogen can lights around the eaves with LEDs. Enhancements will still be going on, we are still looking at the roundabouts. Long term projects we are working on is putting security guards under the CDD and we are working with the HOA on that aspect. Removal of trees on infrastructure, lights and fire hydrants, installation of individual irrigation meters at all homes as well as in clubhouses, long term solution on irrigation issues. We are looking to have the documents changed since they say you are not allowed to have individual irrigation meters. We also have the contract between Toho and Khov that we will be looking at. Mr. Peltier stated next week when they are painting, be very cautious coming in and out of the entrances at the main gate. The reason the gate arms are in the position they are is because they are made to breakaway and the one on the outside of the arm flops and the arm gets locked in behind the controller box. TENTH ORDER OF BUSINESS Adjournment On MOTION by Mr. Peltier seconded by Mr. Rose with all in favor the meeting adjourned at 1:43 p.m. Secretary/Assistant Secretary Chairman/Vice Chairman Landscape Lighting Proposal Licensed and Insured (407) 413-0442 TPGLighting@gmail.com www.TPGLighting.com Client: Windward CDD 2112 Antilles Club Dr Kissimmee, FL 34747 Installation Map Project Renderings Proposed Fixtures Brass Up Light Proposed Fixtures Brass Spread Light Proposed Fixtures Small Brass Wash Light Proposed Fixtures Brass Wash Light REQUEST FOR QUALIFICATIONS (“RFQ”) FOR ENGINEERING SERVICES FOR WINDWARD COMMUNITY DEVELOPMENT DISTRICT Windward Community Development District (“District”), located in Osceola County, Florida, announces that professional engineering services will be required on a continuing basis for the District. The engineering firm selected will act in the general capacity of District Engineer and, if so authorized, may provide general engineering services as well as engineering services on an ongoing basis and for the design and construction administration associated with the District’s capital improvement plan. The District may select one or more engineering firms to provide engineering services on an ongoing basis. Any firm or individual (“Applicant”) desiring to provide professional services to the District must: 1) hold applicable federal, state and local licenses; 2) be authorized to do business in Florida in accordance with Florida law; and 3) furnish a statement (“Qualification Statement”) of its qualifications and past experience on U.S. General Service Administration’s “Architect-Engineer Qualifications, Standard Form No. 330,” with pertinent supporting data. Among other things, Applicants must submit information relating to: a) the ability and adequacy of the Applicant’s professional personnel; b) whether the Applicant is a certified minority business enterprise; c) the Applicant’s willingness to meet time and budget requirements; d) the Applicant’s past experience and performance, including but not limited to past experience as a District Engineer for any community development districts and past experience in Osceola County; e) the geographic location of the Applicant’s headquarters and offices; f) the current and projected workloads of the Applicant; and g) the volume of work previously awarded to the Applicant by the District. Further, each Applicant must identify the specific individual affiliated with the Applicant who would be handling District meetings, construction services, and other engineering tasks. The District will review all Applicants and will comply with Florida law, including the Consultant’s Competitive Negotiations Act, Chapter 287, Florida Statutes (“CCNA”). All Applicants must submit one (1) electronic copy and one (1) physical copy of Standard Form No. 330 and Qualification Statement by 5:00 p.m. on Tuesday, January 13, 2026, and to the attention of Governmental Management Services – Central Florida LLC, c/o Jason Showe/Brittany Brookes, 219 E. Livingston Street, Orlando, Florida 32801; Ph: (407) 841-5524 (“District Manager’s Office”). The Board of Supervisors shall select and rank the Applicants using the requirements set forth in the CCNA and the evaluation criteria on file with the District Manager’s Office, and the highest ranked Applicant will be requested to enter into contract negotiations. If an agreement cannot be reached between the District and the highest ranked Applicant, negotiations will cease and begin with the next highest ranked Applicant, and if these negotiations are unsuccessful, will continue to the third highest ranked Applicant. The District reserves the right to reject any and all Qualification Statements. Additionally, there is no express or implied obligation for the District to reimburse Applicants for any expenses associated with the preparation and submittal of the Qualification Statements in response to this request. Any protest regarding the terms of this Notice, or the evaluation criteria on file with the District Manager’s Office, must be filed in writing with the District Manager’s Office, within seventy-two (72) hours after the publication of this Notice. The formal protest setting forth with particularity the facts and law upon which the protest is based shall be filed within seven (7) calendar days after the initial notice of protest was filed. Failure to timely file a notice of protest or failure to timely file a formal written protest shall constitute a waiver of any right to object or protest with respect to aforesaid Notice or evaluation criteria provisions. Any person who files a notice of protest shall provide to the District, simultaneous with the filing of the notice, a protest bond with a responsible surety to be approved by the District and in the amount of Ten Thousand Dollars ($10,000.00). Any and all questions relative to this RFQ shall be directed in writing by e-mail only to the District Manager, Jason Showe at jshowe@gmscfl.com. WINDWARD COMMUNITY DEVELOPMENT DISTRICT DISTRICT ENGINEER REQUEST FOR QUALIFICATIONS COMPETITIVE SELECTION CRITERIA 1) Ability and Adequacy of Professional Personnel (Weight: 25 Points) Consider the capabilities and experience of key personnel within the firm including certification, training, and education; affiliations and memberships with professional organizations; etc. 2) Consultant’s Past Performance (Weight: 25 Points) Past performance for other Community Development Districts in other contracts; amount of experience on similar projects; character, integrity, reputation of respondent; etc. 3) Geographic Location (Weight: 20 Points) Consider the geographic location of the firm’s headquarters, offices and personnel in relation to the project. 4) Willingness to Meet Time and Budget Requirements (Weight: 15 Points) Consider the consultant’s ability and desire to meet time and budget requirements including rates, staffing levels and past performance on previous projects; etc. 5) Certified Minority Business Enterprise (Weight: 5 Points) Consider whether the firm is a Certified Minority Business Enterprise. Award either all eligible points or none. 6) Recent, Current and Projected Workloads (Weight: 5 Points) Consider the recent, current and projected workloads of the firm. 7) Volume of Work Previously Awarded to Consultant by District (Weight: 5 Points) Consider the desire to diversify the firms that receive work from the District; etc.