This isn't legal advice, and I don't have a real-world example, but some coverage issues to pay attention to might include injuries to common law employees, injuries involving liquor, and punitive damages for gross negligence.Keep in mind that umbrella insurance policies are negotiated contracts like any other insurance policy.

My hang up is 1) I've never done a deal before and I don't feel confident going through this transaction solo at this time.2) I'm not sure what I want to do is legal, or if I need to disclose all of this information to the agent, the other investor or if I should try to find someone to JV with me on the deal. ( If I do JV, how do I ensure I get compensated?)

This will have their full legal name, address and EIN.If they check a box indicating that they are a corporation, then you do not have to send them a 1099, but it does not hurt anything to do so and I always do it anyways.LLCs, Sole Proprietors and pretty much anybody other than an S or C Corporation should get a 1099.

Do not rely on it as legal advice.

If the garage is "deeded" then the legal description of said garage would appear in the deed. 

I'm wondering if someone with experience in self-directed IRA investing could comment on the possible path below (I acknowledge no one responding is providing legal advice, etc. and I should check with a lawyer - I'm just looking for whether going down this path might be possible before calling my lawyer and getting a bill). 

I am still heavily involved in building/yard maintenance and turnover work,  but I leave all the stuff with legal risk (advertising, showing, leasing, enforcement, rent collection, deposits, etc)  to the PM.  

Not an attorney so this isn’t legal advice.My cpa who’s based out of Houston has recommended not doing Series llc.

Due to capital restrictions, I would look into House Hacking.

Any legal issues I would need to worry about with the SEC?