Thought about running a landlord bootcamp for six months and still haven't pulled the trigger

That $300 number is probably fine for a half-day but I'd test $197 first with a hard deadline, just to see who actually converts versus who said they'd probably come. Twelve paying seats at even the lower number covers your time and tells you whether the audience is real before you book a room.

The guys with funnels behind them are teaching generic stuff. You know the specific Q1 ordinance risk in your market and those 40 landlords already pick up when you call, which is worth more than any funnel.

Twelve paying landlords at $300 is $3,600 for one Saturday, which is not nothing.

What's stopping you from just texting those twelve and asking if they'd show up in March for $300 to talk through the Q1 ordinance stuff specifically?

If ten say yes before you've built anything, you don't have a content problem, you have a scheduling problem.

The rent control angle is actually your whole case for doing this now instead of later. Q1 deadline is a forcing function that makes the timing real for your audience in a way that a generic "landlord bootcamp" never would be. I ran a one-day thing in Cleveland in 2021 for about 22 people, charged $250, and the only reason anyone showed up was because I framed it around a specific zoning change that was hitting their portfolios in 90 days. Without that hook it would have been a networking lunch nobody paid for.

Where I'd push back on your hesitation about the "guys with funnels" is that your 40 landlords already trust you with their actual assets, which is not something a bootcamp guy with a podcast built in a weekend can compete with. My mistake in Cleveland was I hired a co-presenter to add credibility I didn't think I had, paid her $800 flat, and she spent 40 minutes on material my audience already knew cold and I lost control of the room for basically half the morning. Cost me follow-on business because three attendees thought the event was sloppy. You already have the content, you already have the credibility with this specific group, the only thing adding a "more experienced" name does is introduce someone whose priorities aren't yours on the day.

The reluctance to pull the trigger on something like this usually comes from comparing your first version to someone else's tenth. Those guys with the funnel behind them did a version once where eight people showed up and half left before lunch. You're not starting from zero though, you're starting from 40 people who already ask you the same questions every winter, which is actually the hardest part of building any paid room and you already have it.

One thing worth thinking about practically: the rent control ordinances in Q1 give you a deadline you don't manufacture, and deadlines are what actually fill seats. I've watched educational events in markets similar to yours either sell out or die based entirely on whether there was a reason to attend now versus eventually. Eight hours on a Saturday might be too much for a first attempt, not because the content isn't there, but because landlords in that $1,450 median range are often managing two or three units on the side of a day job, and a four-hour evening session on a Tuesday in January, focused specifically on what the ordinance changes mean for lease language going into February renewals, probably converts better than a full Saturday bootcamp framing. You can always expand it once you know who actually shows up and what they're still confused about when they leave.

Twelve warm bodies who already trust you is a better starting point than most bootcamp guys have after two years of funneling. That $1,450 median is probably already stale. Two-beds in comparable Northeast mid-size markets I watch have been clearing $1,580 to $1,640 on renewals this cycle, so if your landlords are pricing off that anchor they are likely leaving real money on the table, which is exactly the reason they would show up on a Saturday.