Don’t get involved in their life.

I had 1 transaction with 2 agents involved , long and slow .

The management of vacation or short term rentals tends to gravitate toward the active business side of the equation and that is the real problem with you taking on that level of involvement for your IRA or 401k.

The things that should be in the contract are:The address of the house and legal descriptionThe parties involved:  the seller and yourselfThe price that you are buying it forYour contract is assignableSignatures and dateDeposit amountAny contingency clause(s)

I'm reading all of this (only about half way through) and there is nearly a dozen major violations the company I used to work for are involved in.

They are not illegal per se, just not worth the risk involved when there are other more suitable strategies such as wrapping.

I've read books and listened to podcasts but was looking for a more involved way to fill these knowledge gaps.

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Matt,Speaking toward the insurance piece, your insurance premiums are going to depend on several different factors such fire protection class code, roof age, square footage, age of dwelling, etc.

Within our smallest budget yet we added square footage to the basement, a big third bedroom in the attic and loads of goodies in the kitchen including a custom island we built and quartz countertops we cut!