You should really analyze your options, as data should make your decision easier:)How much have you been making on the STR?

.: You might be able to raise extra capital to support this project by listing the property for fractional ownership on lofty.ai.

Also its my understanding that if he bought the note for lets say 10k  and it had an unpaid balance of say 25k  all arrears and cost including on the opening bid and if it had sold 3P at the sale for say  40k  Bob would get his 25k .. which would give him a 15k profit on the deal and the extra 15k would go to next in line if their were leins or the trustor/owner who lost it. 

I would throw in a few more out there for you like Listing optimization: Rankbreeze and Intellihost, Data Companies: AirDNA, Mashvisor, etc., and guest verification platforms like Superhog or Chekin.

It is 'lost' when investing within a retirement account.2) If the extra rate of return is about 1%-2% it may make sense given all the extra worth involved such as setting up and paying for the SDIRA account and then potentially having to file certain tax forms if your income is subject to Unrelated Business Taxable Income.

It will take extra work at first, but the payoff can be well worth it if you’re up for the challenge.I won't sugarcoat it—BRRRR isn't easy, especially when you're juggling everything else in life.

I just got quoted $160000 for a four unit plus in law in Brookfield including permit and all related fees. for an extra $3500 I can add two EV chargers, but will receive a $16,000 credit from ComEd.

That is a data/privacy issue that could cost them millions.

But my experience is like yours 90% of guests are reasonable, and the other 10% cost me an extra $100-200 for the month stay.

Yes, getting sued is a risk factor and I've been involved with frivolous lawsuits which are not fun, but in my opinion you'd be in a much better spot owning a property in your personal name that let's you keep an extra 10-20% of the purchase price in your pocket as emergency funds, as opposed to buying the loan under an LLC that requires every last penny you might have to make the higher down payment, then you have to operate on a shoestring.