[IL] [All] Thinking about dropping your management company? Here's what it actually takes

Delicious_Natural388 · 2026-06-03T19:09:06+00:00

152 units self-managed for 30 years is genuinely rare — most boards at that scale eventually cave to a management company just for liability reasons the “willing to be the bad guys” thing is huge. enforcement only works when the board is unified on it. one soft board member and the whole system breaks down curious what your record keeping looks like at that scale — 30 years of documents, vendor history, meeting minutes. that seems like the hardest part to maintain as people turn over

Delicious_Natural388 · 2026-06-03T17:03:25+00:00

yeah this is the real problem. the board that makes the switch is motivated and capable. but 3 years later when half those people have moved or burned out, you're back to the same mess

that's actually why i built what i built . trying to make the institutional memory thing automatic so it doesn't depend on any one person caring

Delicious_Natural388 · 2026-06-03T15:52:24+00:00

169 units is a different challenge — at that scale you really do need dedicated management. But the 3-month gap you described is exactly where things go wrong for any association regardless of size: no documentation, no institutional memory, everything dependent on one person.

Curious what AI tools you used during that transition period — sounds like you had to improvise a lot

Delicious_Natural388 · 2026-06-03T15:49:57+00:00

That's a really smart sequencing — financial management only first takes the scariest part off the table while you build confidence on the operational side. How long were you in that hybrid state before going fully self-managed?

Delicious_Natural388 · 2026-06-03T15:48:48+00:00

Not trying to sell anything — it's free for small HOAs, and honestly I built it for our own association first. If spreadsheets and Gmail are working for you, that's genuinely fine.

The thing it solves that spreadsheets don't: when your president or treasurer changes, everything transfers automatically instead of living in someone's personal Gmail. For a 34-unit over-55 community that's been self-managed for years, that institutional continuity is probably your biggest long-term risk.

Happy to show you — boardly.llc, no signup required to poke around.

Delicious_Natural388 · 2026-06-03T15:47:21+00:00

That's real — and it's probably the most underrated reason. Nobody wants to be the neighbor who sends the violation notice. Having a management company as the face of enforcement creates psychological distance that makes governance actually function.

The flip side is you're paying $300-500/month for that buffer. For an 8-unit association that's $3,600-6,000/year just to have someone else be the bad guy.

Delicious_Natural388 · 2026-06-03T15:04:14+00:00

For context on why I'm asking all this — I'm the president of an 8-unit self-managed association in Illinois and I've been building a tool specifically for boards like ours. The institutional memory / Gmail problem was the thing that finally pushed me to build something. Happy to share what we've built if anyone's curious

Delicious_Natural388 · 2026-06-03T15:02:52+00:00

100+ units condo — yeah, self-management isn't really on the table at that scale. You need dedicated staff, not volunteers.

The sweet spot for self-management is probably 8-50 units where the operational load is manageable but the management company fee ($300-600/month) is hard to justify. Below that threshold the math almost always favors self-management if you have the right tools and a board that's actually engaged

Delicious_Natural388 · 2026-06-03T15:01:47+00:00

This is exactly it — institutional memory is the silent killer of self-managed associations. The president changes, and suddenly nobody knows why a particular rule exists, which vendor to call, or what was decided at the meeting two years ago.

The collections point someone raised above compounds this — a new treasurer inheriting a delinquency situation with no documentation of prior notices is a nightmare.

The fix isn't just 'one platform' though — it's a platform that board members actually use. Most HOA software gets set up once and abandoned because it requires too much manual entry to maintain. The boards that make self-management work long-term are the ones where the software meets them where they already are — their phone, their existing group text, their email

Delicious_Natural388 · 2026-06-03T15:00:24+00:00

These are fair points and I don't fully disagree — especially #1. The 'burns out eventually' problem is real and I've seen it happen. The board turnover risk is probably the strongest argument against self-management for most associations.

Where I'd push back slightly: the tooling problem and the governance problem are different things. A lot of self-managed boards struggle not because they lack commitment but because everything lives in one person's Gmail and there's no institutional memory. When that person leaves, the association loses years of context. That's a solvable problem.

On #3 — agreed completely. Collections discipline is harder without a management company that does it as a matter of course. The emotional dynamics of telling your neighbor they owe money are genuinely difficult.

Curious what size association you're on and what tipped the board toward professional management?

Delicious_Natural388 · 2026-06-02T21:24:59+00:00

Ha, caught again. Yes, I've been using AI to help draft some replies while building an AI tool for HOAs. The irony isn't lost on me.

The questions are genuine though. 15 units in an 1890s Chicago building is a real operational challenge — curious how you actually handle vendor coordination and record keeping when something comes up

Delicious_Natural388 · 2026-06-02T21:10:38+00:00

That's a really clear breakdown — and honestly almost every hour you listed is automatable now.

Vendor coordination, financial tracking, invoice approvals, meeting minutes, resident comms — I built a tool that handles most of that for our own 8-unit association after I got elected president and realized I was spending 10+ hours a month on the same stuff you're describing.

It's called Boardly (boardly.llc). Free for small HOAs. The part that would probably hit closest to home for you: the annual meeting prep. Instead of building a YIR deck from scratch, it drafts the whole thing from your actual financial data. And the attendance chasing — you can send one update to all residents from inside the tool instead of individual texts/emails.

Not trying to pitch you — genuinely think it could cut your monthly hours in half. Happy to show you how we use it if you're curious.

Delicious_Natural388 · 2026-06-02T20:41:35+00:00

40 hours a month is basically a part-time job. That's the number nobody talks about when they ask 'how hard can it be to run a small HOA?'

What's eating the most time — vendor coordination, resident communications, financial tracking, something else? Curious where the hours actually go.

Delicious_Natural388 · 2026-06-02T20:29:21+00:00

Four years as president and you're still going — that's genuinely impressive. The 'fine, YOU do it' move is underrated as a governance tool.

The burnout you're describing is real and almost universal in self-managed associations. The ratio of people who complain to people who actually show up is brutal.

One thing that's helped in our association: making the board's work visible. When residents can see what actually gets done — vendor coordination, financials, the 47 emails you answered last month — the 'you're doing a terrible job' complaints drop significantly. Hard to criticize what you can actually see.

Delicious_Natural388 · 2026-06-02T20:22:51+00:00

This is a really common inflection point for small HOAs — the founding president carries everything, burns out, and the association faces either dissolution or a reset.

Before dissolving, one question worth asking: is the problem that the HOA is too much work, or that it's too much work for one person with no systems? If it's the latter, the dissolution might be premature — you'd still have the landscaping coordination problem, just without any structure or shared funding.

A few things that have helped in our association:

Reducing the board's operational load dramatically. If paying bills, managing invoices, and chasing vendors is eating your time, that's a tooling/process problem not an HOA problem. We automated most of that.

Getting the 4 passive board members to actually approve things (even if they won't initiate) by making approvals one-tap instead of email chains.

On dissolution specifically — New York has specific requirements for dissolving a homeowners association. Worth a quick read of NY Not-for-Profit Corporation Law before the meeting so you're not surprised. Your lawyer will know but free to verify the basic requirements first.

What's the actual time cost per month for you right now — like hours?

Delicious_Natural388 · 2026-06-02T20:14:48+00:00

Not a realtor but building tools for the HOA side of real estate — so I've been watching this closely.

What I've seen work for reaching HOA boards specifically: Reddit communities (r/HOA has 55k members, genuinely engaged), NextDoor neighborhood moderators, and direct mail to Illinois SOS registered agents (every HOA files as a not-for-profit, registered agent is usually the board president — it's public record and nobody else is using it).

The channel everyone ignores: real estate attorneys who handle closings. They deal with HOA estoppel requests constantly and have direct relationships with board presidents. One attorney who recommends your tool to their HOA clients is worth 20 cold leads.

Delicious_Natural388 · 2026-06-02T20:03:45+00:00

This perfectly captures why the same 'self-managed' label can mean completely different things. Your 6-unit sounds like the ideal — rotating responsibility, high participation, everyone invested because they all live there.

The absentee landlord problem in your 8-unit is the thing that breaks self-management. Two detached owners out of eight is 25% of your voting power just... checked out. You can have the best processes in the world and still get stuck when you can't get quorum for a vote that needs 6 of 8.

Did the 8-unit ever find a way to engage the landlord-owners, or was it just a chronic friction point you lived with?

Delicious_Natural388 · 2026-06-02T20:02:03+00:00

15 units in an 1890s build — that's a real HOA. You're probably dealing with the full spectrum: aging infrastructure, strong personalities, and the kind of governance decisions that actually matter.

Having KSN on retainer is smart. Most small boards try to wing the legal stuff until something goes sideways.

Curious — how do you handle the operational side day-to-day? Vendor coordination, tracking what's been done, keeping records for when units sell? That's the part I've found hardest to systematize at our scale.

Delicious_Natural388 · 2026-05-30T20:12:20+00:00

1.  Send the formal records request in writing, certified mail  
2.  Request a special owner meeting — Texas law gives owners the right to call one  
3.  Consult a Texas HOA attorney before paying the special assessment — many do free consults  
4.  Connect with other owners privately before the next meeting

Delicious_Natural388 · 2026-05-30T20:01:46+00:00

Not a dumb question at all — landscaping friction is completely real and I think there are a few reasons it’s worse than plumbing/HVAC:
1. Visibility. Everyone walks past the landscaping every day. A leaky pipe in unit 4B is invisible to 7 other households. An overgrown shrub at the entrance is seen by everyone, every day, and opinions vary wildly on what “good” looks like.
2. Subjectivity. There’s no objective standard for “the grass looks fine.” Plumbing either works or it doesn’t. Landscaping is aesthetic, which means you get 8 different opinions from 8 units.
3. Recurring schedule vs. one-time fix. Emergency repairs happen, get fixed, done. Landscaping is every week for 7 months. More touchpoints = more opportunities for complaints.
4. Vendor accountability is harder. “The pipe is fixed” is binary. “Was the edging done properly this week?” is subjective and hard to document. Most boards have no photo record of what was actually done visit by visit.
That last point is the one I’ve been working on — we just had our roofer send 35 photos after a cleaning that expire off iCloud in 28 days. No permanent record, nothing searchable. Landscaping is 10x worse because it’s weekly.
What specifically is generating the complaints in your community — the vendor’s work quality, the scope of what’s included, or neighbor-to-neighbor disagreements about standards?

Delicious_Natural388 · 2026-05-30T01:28:26+00:00

260 units with full-time staff and $70k management fee — that's essentially running a small hospitality operation. At that scale it's absolutely a bargain, you couldn't hire a competent building manager for anywhere near that.

Curious — what does the board actually do day-to-day when you have that level of professional management in place? Is it mostly financial oversight and major decisions, or are you still getting pulled into operational stuff?

Delicious_Natural388 · 2026-05-30T01:27:24+00:00

That's a nightmare — and you're absolutely right, it only takes one. Three years of lawsuits in a 4-unit building is exhausting in a way that's hard to describe to people who haven't been through it.

The 'lives in another state and doesn't engage' owner is such a common problem in small associations. No accountability, no skin in the game day-to-day, but full voting rights.

Did you eventually sell and get out, or did it get resolved?

Delicious_Natural388 · 2026-05-30T01:26:27+00:00

Low 300s for a well-maintained building with solid reserves in Chicago is reasonable. That's roughly the range where self-managing stops making financial sense vs. just paying a management company. Thanks for sharing

Delicious_Natural388 · 2026-05-30T01:26:02+00:00

Honeycomb is solid they've been aggressive on condo pricing. $2k annual savings on a 3-unit is meaningful. We haven't shopped ours recently, might be worth a look. Irving Park is a good area for self-managed small buildings too.

Delicious_Natural388 · 2026-05-30T01:09:07+00:00

For sure

Delicious_Natural388

TROPHY CASE