I asked this very question to former head legal counsel of well-known title company here in CA.His answer: “It depends.”That was helpful.As the prior poster indicated, each of these cases are unique and have their own facts and circumstances.

Some lenders offer unique solutions and programs for your specific situation.

Personally, I would only purchase for STR right now on either very unique/special properties or on those that also work out as LTR.I am a licensed REALTOR who is investor focused.

They don't always account for differences in finishes, location nuances, or other unique property features.

Our system is a bit unique.

They have been buying Greek junk bonds lately along with all kinds of other oddball and unique investments.

Each of these have their own attractions and draws and unique activities. 

Do you need unique checks and balances in your away market so someone is representing your interests in the away market--yes.Slow and steady wins the race.  

Now, we do live in a small town, touristy area that does lack in nicer/unique short-term rentals. 

I don't have any answers for you Holli but I'm commenting so I get notifications when others reply to this as it sounds like a unique project and I'd love to hear more!