I've not heard of anyone having success with cold email since it all goes straight to their spam folder or they delete it if it makes it to inbox.but for the people that actually get the email, it's all about that subject line.

(not even sure if paying us a commission on insurance is "legal")Or are there products / marketing techniques we can use with our captive audience (without spamming them?)

You are gambling.

That’s the gamble...

I guess it’s all a gamble really.

I want a linear market because inflation adjusted appreciation is a gamble, no one knows where the markets going.

The only way I would consider what you are proposing is if the equity from your coop is enough to place enough of  downpayment (think 50% of purchase price) on a small multifamily (think 3-4 family) so that the income from the new property is enough to cover all expenses of the new property as well as the loan (or a significant percentage thereof) on your personal residence.It's a gamble that can break you or be the beginnings of your real estate portfolio.

B) I will never look at any future deal, ever, your loaded into spam engine and "poof" annoyance solved.

Ours were plausible triplexes BUT there was a bit of a gamble involved.

Very few have been operated as a business...most are, at best, a hobby, where the Owner enjoys doing handyman work (often of dubious quality), at worst, an absolute "investment" Gamble, with no regard for tenants, laws, or much of anything but spending the absolute minimum while collecting the most money possible until their "cash cow" implodes.