It doesn't appear my wife will have to pay anything, her brokers insurance is handling it. 

Insulated cover with ICF in ground walls keep heat in when not in use.

We have an acquisition team that finds properties for you;we connect you with vetted team on the ground like property manager, contractors; we also connect you with HML.

the period of time it was investment you will pay tax on. 

Would renters be willing to pay $2,600 a month, or would they be more inclined to purchase a home instead?

Pool for sure... but probably way more $$ depending on what you area actually adding...above ground I assume...

You have a lot of properties around the colleges as well that can be rented to students or since its next to a couple of Hospitals the Nurses, Doctors, and other medical staff pay good rents.

Apartments.com makes money by landlords paying to make their rental listings "premium" to get bumped up in search results.

Do you find someone on places like craigslist to get "boots on the ground" to look at the property and assess any damage?

I'd rather trust that someone pay an assignment fee (based on your word of mouth referral) and not get paid then the other scenario.