The list of documents mentioned by Matthew, Kenneth, and Patrick is spot on.

I have tenant applications with paystubs and other documents requested.

My wife is an insurance agent (in FL) and I sell to a lot of clients using a second home loan. 

• Any insurance that protects AFTER closing (completed ops, E&O, etc.)?

He failed to pay on his property insurance so I had to purchase forced placed insurance on the property. 

Cycle 4 Mandatory Restatement The IRS requires pre-approved plan documents (used by most Solo 401(k) providers) to be completely rewritten every six years to incorporate cumulative law changes.

Proper is the only insurance company that so far will insure, but only as their standard commercial STR policy. 

STR-specific insurance isn't about "worth it."

I just had an insurance company approach me about their client wanting to rent my house. 

But lender's internal underwriting rejected that insurance.