But the evening while congenial was also light on substance with softball questions like What has the town done right/wrong? and What leadership qualities would you bring? Left unexplored were key issues facing Windermere residents like the 7.20 percent increase in millage rate; the $453,000 in legal fees the town has paid to date to fight over the boathouses — with another $225,000 budgeted as the lawsuit proceeds to trial; or how the town might close the budget gap for school resource officers at Windermere Elementary School if Orange County’s School Board doesn’t increase its share of costs. 

Here's what got the most attention:

Leadership qualities

When asked what skills and qualities they would bring to the town council, both David and Davit highlighted their experience serving on the town council for the last four years.

“Additionally, I'm a civil engineer,” Davit said, “so what does that mean to everybody? That means I know how to solve problems.”  

David mentioned working for Congressman Daniel Webster (R-Clermont), who represents West Orange County, during the 1980s when he was in the state legislature. She said her communication skills as a sign language interpreter with her own agency, JFD Communications, is also an asset. Krens also talked about his communication skills from experience serving on Windermere’s many boards and committees, such as the Tree Board and Long Range Planning Board. 

While Lee said she does not have experience serving on Windermere boards or committees, she said growing up in town is “considered a skill or an asset to really understand the town.” She said she’d bring negotiating skills from her position as vice president of sales and marketing at her family’s company Techmounts and noted she has been involved with the Legal Aid Society. (She is not an attorney.)

David and Davit said neither had served on a Windermere board or committee before being elected. Davit added that he “was foolish enough to come right into town council,” although he has since joined other unrelated boards. Stroup said it was the "willingness to serve" that was essential.

Stroup tied his previous position, working for more than 30 years as an Orange County Sheriff’s captain and SWAT commander, to his role as council member. He said he leads by example even from a position of authority, putting in whatever work is necessary to address an issue.

“I repaired the doors on this building [Windermere Town Hall]. I repaired the schoolhouse, so I see leadership by example,” Stroup said. “I don't ask anybody to do anything that I have not done or not willing to do.”

Traffic 

Candidates found easy agreement that the biggest challenge facing Windermere today is traffic. To better manage traffic within Windermere, two main solutions were discussed: redistribute traffic within the town or prevent traffic from going through it. 

“I just don't think realistically we're gonna be able to say, Go! Get away!” David said. “Selfishly, I would love to be able to do that.” She ultimately agreed that facilitating traffic flow through the town would be the better solution. 

Davit, who said he wants to “get traffic out of town,” noted that much of the traffic isn’t heading for Windermere — it’s pass-through traffic on its way to Horizon West. He's Windermere’s liaison to MetroPlan Orlando’s Municipal Advisory Committee, and he said working with regional groups on ways to divert traffic out of the town is the solution. He said there’s already construction to allow commuters to bypass Windermere and access State Road 429 to get to Horizon West., 

Krens recalled that former Mayor Gary Bruhn had advocated for a “connector from [State Road] 535 to Apopka-Vineland [Road]” with help from Orange County. Krens said he’d like to “resurrect that plan.”

However, Stroup later said the connector plan was a nonstarter because residents would never allow a bypass to go through their neighborhoods.

Lee agreed. “Putting a road over or through these fancy neighborhoods, or anybody's neighborhood, I don't think it's a good idea,” she added. 

Stroup said diverters and roundabouts have already helped alleviate speeding and noise. He added that there are more spots where diverters can be placed. In addition, both he and Lee suggested beefing up the police presence to crack down on speeding. 

“Many of us residents have noticed that there has (sic) been less blue lights around town than there used to be,” Lee said. “People were afraid to go two miles an hour over [the speed limit], and over here, you knew you were going to get a ticket.”

Town communication 

Candidates were split on town communication. David said communication is something the town has done well in recent years, citing Windermere’s use of door-knockers to inform residents about new projects and using the town’s Facebook page for updates. With Town Hall renovations underway, David said she “love[s] the fact that we had the residents come in and give ideas with the kitchen and the bathrooms.” 

Davit, however, called for “over communicating” with residents and said the town should ask residents for their input more often. He cited resident disapproval of the downtown pavilion that came after the project was designed. He said “communication is a two-way street” and encouraged residents to reach out to him. 

Lee also thought the town could do a better job of notifying residents of town council activities. But she added that the onus was on council members to go to residents. “As town council members, it’s our duty to go around and speak to residents and really get input ourselves instead of relying on people to come out to meetings.” 

She said she wants to be a voice for the “dirt roaders” — those on downtown Windermere’s unpaved streets. Issues like the pavilion project and the new annexation of neighboring Chaine du Lac exposed a fissure between residents who live in the “core” or original part of Windermere and those who live in the outlying neighborhoods. 

Failed pavilion project 

Although last year’s failure of the Healthy West Orange/Rotary Club pavilion project was not directly broached, candidates referenced it a few times during the evening, circling back to the unsuccessful attempts at a compromise that cost the town a $1 million grant from the Foundation for a Healthier West Orange to Windermere Rotary Inc. in early 2024. 

“One of the recent issues that came up that I thought we could have done better on was the pavilion project,” said Davit, who brought up the matter unprompted. “We thought we had residents' consensus with the way ahead that we were doing, but when we started asking questions and getting thoughts … we got a little sideways there, we didn't probably communicate enough or solicit enough input from the different residents.”

Originally, the grant was earmarked for a pavilion project near the intersection of Fifth Avenue and Main Street, but there was pushback from some residents who said they didn’t want an events center that would attract more visitors, noise, trash, traffic and parking problems to the downtown. The opposition tanked the project. Subsequent attempts to repurpose the grant for needed Town Hall renovations were also unsuccessful. 

Krens, a past president and member of the Rotary Club who has spoken often about his disappointment in losing the grant, said there were early warning signs that compromise would be necessary for the project to succeed. 

“I'm an engineer by training, and one of the things my training says is a good decision process is seven steps. … [F]or a town like us, I think there's probably an eighth step — consensus,” Krens said. “Without one consensus, our decisions don't stick. We’ve made some that didn't stick. I'd like to see, for the crucial decisions, us actually work through the seven-step process, or at least enough of those seven steps so that we made sure we did it right.”

Historic boathouses 

Once Levine was finished with his formal questions, residents came out of the gate swinging, asking candidates where they stood with regard to the long, contentious legal battle between the town council and owners of the five historic boathouses in the Palmer Park lagoon. The current legal fray concerns the town’s decision to terminate the owners’ month-to-month right-of-access leases in March 2022.

The town council has steadily increased its legal budget to litigate the matter. In fiscal year 2022-2023, the town council budgeted $85,000 for legal services but spent $138,227. For fiscal year 2023-2024, however, the town budgeted $100,000 and spent $314,830. For the current fiscal year, which began Oct. 1, the budget is $225,000. Since the matter couldn’t be resolved through mediation, a non-jury trial is scheduled for August. 

While the three council members didn’t get into a detailed discussion about the town’s steadily rising legal fees, they were surprisingly forthcoming given the pending litigation. 

Davit answered first, saying the clash began in 1986 with the town council issuing a “resolution” over the boathouse ownership with a 15-year lease. (The validity of that original lease is part of the issue.) 

“After the 15 years, the intent of the town council was for the boathouses to be reverted back to the town to determine what would happen with them,” Davit said. “They extended that lease to 2021, so in 2021 we picked up the challenge again after several decades to resolve what's going on with the boathouses.

“But, honestly, I don't care what happens as far as determination of ownership, whether it's the residents of the boathouses or the town. What I don't want to happen is for my kids to be sitting up on town council in 20 years trying to resolve the same issue,” he added.

Krens said he agreed with Davit’s position and felt that the issue was no longer in the hands of the town, but in the hands of lawyers. 

“What the town council does from this point on is probably moot. I've been on both sides of the issue,” Krens said. “I'm with Tony, I'd like to see it resolved … I’m with whatever the court decides, hopefully to be done quickly.”

Lee was more direct, supporting the boathouse owners and expressing dismay in the amount being spent to cover the cost of the lawsuit. 

“We all know that if you can't prove ownership of something, you can't then go and write a lease for that property,” she said. “We need to figure out if that original lease was actually valid in the first place because if it wasn't valid in the first place, this entire thing goes away. Second … town council members do have the ability to put a stop to this, so they can come together and vote and say, We're done. We don't want to spend any more money.” 

Stroup, candidly said he’d hoped the matter would have been resolved before he took his seat on the town council two years ago. He said he “tried to ignore it” but when he looked into it, he found he “had an issue with whether the lease is even valid at all” even as he hoped for reconciliation between the town council and the boathouse owners. 

“I want to know what the original intention was when it was handed to whoever it was handed to,” Stroup said. “I don't know the answer to that, but if it belongs to the town, then it belongs to the town. If it belongs to the residents, then it belongs to the residents.

He said he does not want to go to trial because the “cost of the trial is gonna be another half a million dollars combined, I'd love to see it resolved before trial.”

David said they ultimately “need a decision.” 

“We need to know and the judge will be able to tell us from all the information that he has and all the people who are telling him the information and all the documentation that he's received from our lawyers and from their lawyers," she said. "I think it's just better to know, and then we can just go on and be amicable with everybody and get along.”