Boards
Landscaping costs a stupid amount of money.
So does repaving a parking lot, replacing a roof, and fixing a drainage issue nobody noticed until it became everyone's problem. Board work is basically the art of deciding what matters, when, and how much you can actually afford to spend on it.
Last year I helped raise Wyndham's HOA dues by 15%. My dues went up too. People were not thrilled. But the alternative — deferring the maintenance and reserve contributions that keep a 105-unit community running — would have cost everyone a lot more later. That's the job. You make the call that's right for the community, even when the community isn't happy about it right now.
Board work is about making good decisions for people who didn't ask you to make decisions for them, with money they'd rather keep, for problems they can't see yet.
I've been doing this work at Wyndham for several years, and I've learned a lot — about finances, reserves, vendor relationships, community communication, and how to stay grounded when the decisions are hard. Here's some of what I've figured out.
What I've learned & what I've done
Reserve studies sound boring until you realize they're basically a 30-year financial plan for your community's physical infrastructure. Understanding how to read one, how to fund it appropriately, and how to explain it to residents who just want to know why dues are going up — that's a real skill.
My experience
I've worked through reserve study cycles at Wyndham, managed relationships with our savings and operating accounts, and helped the board make funding decisions that balance short-term affordability with long-term sustainability. I've also had to be the person who explains those decisions to residents — which is its own challenge.
A property management company is a partner, not a substitute for board engagement. The boards that struggle are usually the ones that either micromanage everything or completely check out and let the management company run the show. The sweet spot is somewhere in the middle, and it takes a while to find it.
My experience
I've worked closely with Wyndham's property management company on vendor coordination, maintenance prioritization, and day-to-day operations. I've learned how to ask the right questions, push back when needed, and trust the process when appropriate.
Most HOA communication happens reactively — something breaks, someone complains, the board sends an email. The communities that run well are the ones that communicate proactively: here's what's coming, here's why, here's what it means for you.
My experience
I've built community newsletters, surveys, and preventive announcements for Wyndham — things like condensate line cleaning reminders before HVAC season, water leak detection guidance, and project updates that give residents real information instead of vague reassurances. Communication is one of the highest-leverage things a board can do well.
Nobody tells you when you join a board that you're going to make decisions that make your neighbors angry. Dues increases, parking enforcement, noise complaints, policy changes — at some point you're going to have to make a call that not everyone agrees with. How you handle that — and how you stay grounded in what's actually right for the community — matters a lot.
My experience
I've been through dues increases, contested decisions, and the kind of community tension that makes you wonder why you volunteered for this. I don't have a magic answer, but I have perspective — and I'm happy to share it with anyone who's in the thick of it.
Beyond Wyndham
Columbia Association is a weird super-HOA that serves the entire planned community of Columbia, Maryland. As board chair, I've navigated large-scale governance questions, CEO performance evaluation, ethics proceedings, and the particular challenge of leading a board of elected representatives who don't all agree with each other. It's a different scale than a condo association — but a lot of the same principles apply.
If you're on a board and trying to figure something out — finances, vendor relationships, a hard decision, whatever — I'm genuinely happy to talk it through. I don't have all the answers but I've been around long enough to have useful perspective. Send me an email at collin@collivan.com.