As someone that over analyzes things as well, I’d suggest you step back and think about what your goals are in order to help determine what path to take.I like JD’s suggestion about reinvesting in your business.

Being out of state, I would suggest vetting your "team", meaning find an investor realtor, lender/s (hard $ / long term), property manager, contractors, etc.

If you personally are having trouble making a profitable deal, make a post and ask for suggestions.  

My suggestion is to simply file the BOI requirement.

I don't use Stessa and never have so I don't know what's going on, but I suggested they take a look at Baselane, which is what I use.

Suggested to do that earlier than later, so there is no liability on a tenant who is not on the lease paper.

Suggestions on learning more about contract for deed?

A few things I’d suggest as a local investor:Know Your Markets: New England is a mix of urban, suburban, and rural areas with very different dynamics.

In short, having all the conversations and commitments in strategy, setting up LLC and all the fun docs of who's doing what, and I'd suggest even getting initial funding into account for at least EM. 

The Hilltop Mall (standard shopping mall, Macys, JC Penny, escalators, if you were alive in the 90s you know),  in Richmond CA was purchased in 2021, but the buyers aren't doing any of our brilliant peanut gallery suggestions.