They both have some more strict STR regulations than I would be comfortable with.

You would be violating the law for doing that.Be comforted that most prospective residents don't provide proper ESA documentation. 

I have comfort that their legal team checked off the necessary boxes. 

In short - here are the reasons I pivoted to Real Estate Investing:All the benefits of Real Estate + growing STR optionsInflation raging at 10%/moCurrency wars and what or who will win them (Prec Metl or CDBC, etc.)Equities markets receive derivative pressures from credit markets and pressures on US dollarRealistic 10+ year opportunity in using Creative Financing, given monetary policies.Global disruption and impact analysis of COVID to businesses (small/large) and individualsWhat I was (originally) looking to get out of the program:Better understanding of Real Estate and it’s MarketLocally like-minded ppl that are more about collaboration than cannibalization (not reflective of BP in any way – this community is great too)Improvement in comfort level working in REI and learning “on the job”A community where I could find deals, connect with ppl for help and ask questions, etc.Business and Corporate Structure recommendations to accommodate short-term & long-term investment strategiesAnonymity strategiesAccess to vetted contracts for traditional, creative and gator (EMD) Real Estate dealsMy experience and feedback based on my expectations:Great original 6 week mentorship program.

Get out of your comfort zone.

If your PM is comfortable with it, then I would say its a good idea. 

They ended up selling at a loss and learned a valuable lesson the hard way.If you wouldn't feel comfortable living in the area, then why invest there?

They are very transparent about where the money goes and great stewards, of it so we feel comfortable giving knowing they're not using it for frivolous excesses. 

It took me a while to get comfortable with 30y mortgages.You have to learn how to control that.

I don't know, I usually get 3 bids and go with whom I'm comfortable with, it's less heavy lifting in the end that you have to do anyway.