I even have a friend who received an unfounded complaint from a neighbor (the neighbor was just against STRs, no events/parties that occurred), and now their property is temporarily banned/under review, regardless of them abiding by all rules.

Dont cut corners just because they're only staying for 2-3 months

So for the Comps you make to arrive at your ARV something that jumped out at me was the adjustments.

Quote from @Dylan Jeluso: This questions is the same question as getting your real estate license when doing flips, you have access to the MLS, you save money on the commission, and you have a little bit of a competitive advantage over the next person that is not licensed.

I've reached out to lenders here on Bigger Pockets- but their rates & terms seem high (DSCR or just not good terms)- I qualify for a conventional loan, but my DTI is almost maxed so why pay an extra 2-3% DSCR when I don't have too. 

These loans are structured a bit differently than conventional loans; the borrower pays the origination to the loan officer instead of the lender paying them, so it’s an up front fee.

My plans would require the Village to rezone the property.

Do you get an inspection and just let the potential seller say they need to wait for that to be done, or do you hire a GC to give you an estimate?

Your Property Manager knows what they're doing and you should just let them work their process.

Why would you recommend someone to go into one of the other?