(More than or less than 1 year)- Were/are the shares from a stock purchase program like ESPP, RSU, ESOP, or something of the like, or were the shares just in a brokerage account at Computershare?

We cut owners all the time who do this or ones who scream at me, our staff or just call us up to crap on us if something wasn't done how they wanted it.

You can save the funds for emergencies or something more pressing.

You want the insurer to be locked in to defend anyone who is operating that rental if they're named individually for something they did or did not do while operating it

Sometimes the issue is they just need something they can use their loan on and a lot of our options are fully renovated and priced over their reach or need so much work.

@Nicholas L.Of course, additional rules won't protect 100% but at least something to use if anything goes wrong because my last tenant cost me more than 7K to repair. 

You're going to pay for the repairs anyway - and that is the most substantial part of the cost and the biggest part of the effort when something big happens - not the property management itself.

What are some things I should look for in the contracts?

Also, what generally defines the line between something that would be filed against the homeowner's insurance vs. the renter's insurance?  

Principle paydown is something that a lot of people gloss over, but your interest rate and loan balance play a big part in this.