And if you dont actually do that, as @Matthew Paul said, the Baltimore States Attorney was just arrested and convicted of mortgage fraud for not meeting occupancy requirements of a loan for a property on a short term rental.

"IF" this is inspected work the building inspector probably isnt going to allow ANY window in a tub shower period. 

Recently, Sevier County TN commissioners voted to require a "permit" for all short-term rentals in the county, "to ensure that all short-term rental units in Sevier County meet minimum safety standards." 

@Yang Zengsub 60K properties in random areas that you don't know well and don't have a strong team in will not cash flow. period.

Our goal is to (eventually) have a second property where we can spend time at our retirement, and that can generate some income as a short-term rental for a portion of the time when we're not using it. 

This building will have 8 apartment units, 5 short-term rental units, and 2 office spaces. 

The rehab must be certified by the National Park ServiceA “certified rehabilitation” means any rehabilitation of a certified historic structure which the National Park Service has certified to the Internal Revenue Service as being consistent with the historic character of such property or the district in which such property is located.In short: no, it's not as easy as writing off 20% of any rehab that you do on some old building.

You can contact other lenders, and do things like DSCR , but they will be more expensive in the short and the long run. 

So I guess the most important questions would be, are you planning on renting it out to an RV owner short or long term?

Tax considerations involve a lot of personal, specific considerations so you are on the right track going for a CPA (make sure they are familiar with income properties and short term rentals).STR is a business and involves "active" income versus "passive" income associated with typical long term rentals.A few general things:1.