My plan would be to keep the front waiting room as a small commercial space and the back offices as efficiency units or studios. 

Meaning that if you fund a $5K EMD and then decide not to close you lose the EMD, or you pay for an inspection up front and risk missing out on the deal while you're waiting for the report.

I will mention that a hot tub could really increase the frequency of bookings. 

Looking my insurance policy it mentions that I can opt for settlement under Actual Cash Value vs Replacement Cost. 

I've worked with several loan servicers, and no matter who you use, it's not fun setting it up, but I've had easier success communicating with OnePoint.They have a login portal to track payments etc, like you mentioned. 

As @Eli Konig mentioned above, going into RE right now without a lot of experience and without knowledge of a local market I think makes TK a decent beginning option.I've been in communication with REI and going through their process right now.

prices are high, interest rates are high, there is tremendous demand for inventory, and - one thing that doesn't get mentioned enough - a record number of properties are debt free. 

The other cities you mentioned should be fine also.

This is what I do currently but it's a process of purchase, rehab, wait 4-6 months, refi, then wrap and sell (and risk DOS clauses).

I can’t wait to share updates as I start this journey!