I've done all of the above, so DM me if you'd like to discuss in more detail.

It does appear that we need more information about actual ability to pay the rent but in reading between the lines it appears that there will be two more adults living in the property, so we have more information to gather.

So, I would say if you want to run a short or mid term rental, keep the furniture but if you want to do long term rentals nix the furniture.

If so, I'd look into that before a DSCR loan to avoid the prepayment penalty DSCRs carry.

I would also hit up meetup.com   In person networking will add so much knowledge and insight.   

A 100-year-old home with structural concerns could mean costly repairs, so get a thorough inspection, especially for foundation and floor issues.

Great idea because like you said, coffee is important to so many. 

So if you had a $100k gain and did an exchange from a $900k property to an $800k property you would owe the same taxes (on the $100k gain) as not doing an exchange. 

Same w/ the folks down at planning & zoning, they're super helpful. i'm in knoxville so happy to talk property specifics. sounds like a cool play. you'll be fine as an owner occupant and city STR rules.  

For many years we did have turnover every year, so that was a good number.