If you deed a property from your personal name to an LLC - especially a disregarded entity - it doesn't really do anything for taxes or asset protection.

In my opinion, you want something that will protect you, but is also understandable for everyone signing.Keep in mind that at the end of the day, here in Illinois, the state is generally contractor-friendly in the court of law, so making sure you document everything clearly with payment will protect you against any potential mechanics liens.We have had several projects that did not go perfectly here in Chicago because we overpromised and didn't keep tight enough documentation. 

Posting on random/obscure booking sites will probably only account for 1% of overall bookings. and the vast majority will come from the big players (Airbnb, VRBO, etc). 

Quote from @Mike Dawson: An LLC is useful for two things: anonymity and legal protection.

So even if you pick a state with stronger protections like WY or NV, the cause of action arose in the state where the tenant fell, so likely that the court where the accident happened would have jurisdiction.

In fact, I’d always protect a broker.

Instead I would just need to do the title search first, then once I pay the down payment file a memorandum for the amount I paid them, and then record the purchase and sale contract/land contract with the county so it's on record and clouds the title for extra protection.

The buyer does not need to use that particular lender, they are simply trying to protect their clients interests the best they can.Go back to your lender and get the pre-approval letter, else your offer will likely not be accepted.

Keep in mind, even with this strategy, reassessment might still occur in the future.For a 100% seller-financed deal, ensure the terms clearly state the tax responsibilities and get expert legal advice to protect your interests.

I'm interested in learning what others in a similar situation use for asset protection from potential lawsuits.