A landlord bootcamp that has sat on the shelf for six months is worth examining

That $300 number is probably fine for a half day, though I would test $197 first with a hard deadline, just to see who converts versus who said they would 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 operators with funnels behind them are teaching generic material. You know the specific Q1 ordinance risk in your market, and those 40 landlords already pick up when you call, which carries more weight than any funnel.

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

What is stopping you from just texting those twelve and asking if they would show up in March for $300 to talk through the Q1 ordinance material specifically? If ten say yes before you have built anything, the problem is scheduling rather than content.

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. The people with the funnel behind them did a version once where eight people showed up and half left before lunch. You are 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 do not have to manufacture, and deadlines are what actually fill seats. Educational events in markets similar to yours tend to 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. The content is there; the constraint is that 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 are still confused about when they leave.

Twelve warm bodies who already trust you is a better starting point than most bootcamp operators have after two years of funneling. That $1,450 median is probably already stale. Two-beds in comparable Northeast mid-size markets 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.

The framing of "bootcamp" is where I'd push back. You're not a coach and positioning yourself as one next to guys who've been running funnels for years puts you in a comparison you don't need. What you actually have is a closed-door Q&A with someone who works their market daily, and that's a different product entirely, one those polished guys can't replicate because they're not in your zip code pulling comps in November. I'd charge more than $300 for that, not less. If the rent control stuff hitting Q1 is genuinely actionable intelligence, $500 to $600 for a half-day with 12 people who already return your calls is a realistic number, and you're still only looking at maybe $6k gross for a Saturday. Run it once, record it, see what questions you didn't anticipate, and decide after that whether there's a second one worth building out. Six months of thinking about it and you've already written the content apparently, so the bottleneck isn't material.

That $1,450 median is low, two-beds in Providence and Hartford are clearing $1,650 right now.