As I see it in the current market, STR is now a way to get a really good, appreciating asset to pay for itself, not a way to produce a meaningful amount of cash flow after all expenses. 

Sometimes I have trouble remembering what day of the week it is!  

Purchase price up to $300k.That way you will have a property that produces passive cash flow every month and appreciates slowly and steadily over time.

Quote from @Markus Samuel: I’ve found a “deal” but I’m having trouble understanding if this is a good fit for me.

I mentioned these specifically because the people running them have high integrity and what I would caution people on is all the new debt funds popping up that are being used to fund their other ventures that are in trouble.

I feel the padsplit model might not be that sustainable if it is that easy for the hosts to have legal troubles.

Other distractions include non income-producing activities - aka any distraction pulling you to do something other than speaking with and following up with people.How can I prepare myself?

Have seen owners of condo's and co-op's get into trouble running an AIR BNB out of a co-op.

When the money dries up, they'll leave just as quickly as they arrived and you may be stuck with a real mess.If it can produce more money as a short-term rental, do it yourself.

I would decline if they have trouble answering the longer term question and it would probably be for their own good.