But…There’s ZERO chance I would rent by the room for $600/months more.

The systems you have in place to handle leads, follow-up and your sales processes are also huge factors.Another factor is what is your monthly marketing budget?

Expected sale price?

Some facts/info you may already know but if not:1) You assume the loan from the servicing bank, meaning you will work directly with the servicing bank.You assume the loan amount, but still need to come up with the difference of the VA loan amount and the sales price, in your case 172K. 2) No one will finance the entire remaining 172K amount.

So it's more-so there a construction/maintenance company, who uses a PM offering as a lead gen and capture device to drive sales. 

As has been mentioned, try to find a way to keep as your primary for 2 years, and all gains are tax free at the sale.

It will be about 3% of tax value which is the sale price in a recent sale.

How would the situation differ with a home that’s never been a STR but would become one, or a home that’s for sale now that is a current STR.

Currently we are seeing STR owners posting for sale due to reduction in prices they can get per night and the vacancy rate increasing. 

That he can weather for 10-15 years, but not 3 at 25% down with $25k in reserves($300k in sale price would afford).