Keep it simple and form an LLC in the state where the real estate is located.

This is simple.

That's the simple reality of it.

Pretty simple when we have this happen. 

Quote from @Ryan Dunner: It's very simple math.

For argument's sake, and to keep the math simple, let's say you have $1 Million in ETF's or some other safe-ish, well-diversified assets.Step 1:  Take out an SBLOC (Security backed line of credit) on said portfolio. 

I do not think it will be nearly as simple as a "drop" or "crash" of any kind.

Just because you add an ADU doesn’t mean it’s going to add enough value to recapture that $300K.If it sounds slightly out of your comfort zone a simple conversation can be extremely impactful Thats where breaking down the payment management tools, local experts on small repairs, credit and background checks for renters, all comes into play.

Not exactly sure where to look for this and have done some googling and asking around but don't have a clear answer for how folks have managed keeping the books clean and everything paid on time in a simple manner!

For us it varies by market but in our primary market 15% plus a small monthly fee to help cover software costs etc if it's a lower gross property.That's full service, host doesn't have to worry about anything and can forget the property even exists if they want to.We do have tiered services where it's 10% (w/ no or lower monthly fee) if the owner wants us to only do one side of it (either manage bookings but not guests/cleanings/maintenance, or vice versa).25-30% used to be more normal but that's legacy pricing now, for a couple of reasons.1) Of course margins are much thinner for owners now that revenue has generally come down across the board from the peak, while home prices and interest rates have risen alongside that.2) Probably even more important, a simple supply/demand equation, particular to the case of increased supply.