Once you pay it off, it goes back to normal relatively quickly (within 1.5 months).

We have a huge influx of people buying in NH at the moment, obviously mostly short-term COVID-related, however I do feel this will be pretty sustained, now that so many people are questioning city life and have realized it IS possible to work from home, so why not do so in an incredibly beautiful place with hardly any crime and tons of outdoor activities?

It sounds like you would benefit from hiring a real estate agent to represent you.

It isn't a large sum in absolute terms, but relative to the rent you made, its significant and I could see someone wanting to pursue a story.

Assuming it's written in your management agreement somewhere that states the owners are current on all financial responsibilities related to the property, does anyone require them to actually provide a current mortgage statement, HOA payment record, taxes paid, etc..... at least at the time of the original management agreement signing.Recently had a new owner sign the agreement, only to find out after we had secured a new tenant for them, that they were in financial distress to say the least (inquiring about bankruptcy) .

This means that if anything goes wrong with the property—like a tenant getting injured or a lawsuit related to the rental activities—the LLC, not you personally, would be the one held responsible.

There are seven tests, however the most relevant tests for STR investors include:Perform substantially all the work related to the activity.Participate over 500 hours during the tax year.Participate over 100 hours during the tax year and no one else participated more.If your property meets one of the exceptions above AND you meet one of the above tests, you can qualify to treat your rental activity as non-passive.

Here are things that would not transfer with a sale:-2.5% interest- prop 13 property tax benefit is saving ~$40/monththese are awesome advantages that are tough to match   In addition you have achieve outstanding return from the appreciation since purchase.On the other hand, you have $300k of equity which places the LTV at ~65%.  

But, again, if you friends  in Indy know a thing or two about investing and can partner with you, where you both have a financial stake and they get "more" of the pie relative to their equity contribution in order to oversee the success, that would be the ideal scenario in my book.As for broadly in markets, both are considered pretty good.  

@Yonah Weiss what do you mean when you say “ tax benefits are gone”.