That seems like an expensive roof - does it need to be completely torn up and rebuilt to hurricane standards?

We sold our (primary) home recently.

In today’s market most homes will be worth more than their outstanding loan balance unless they are VERY recent purchases with little to no money down.

What's his home improvement contractors license?

They’re requesting what feels like an unreasonable amount of information, and the demands keep escalating.So far, they’ve asked for:A video tour of my home officeCredit checks on me and my partnerCopies of the deeds for every property we ownA copy of my partner’s home lease and utility billsBusiness phone billsA signed letter from the bank verifying our accountsBank statementsHonestly, it feels more like qualifying for a loan than trying to become a customer.

The home was built in 2006, great neighborhood, close to the highways, close to everything new that is being built, close to a military base.

Most likely it would be around 150kish - so why pay 180k for a 150k home in that instance?

This home is located in Anderson, IN.

The last thing you want is to have a home run deal that theoretically should be a high-profit flip but is ruined because your contractor screws you over in some form or fashion (late deadlines, inaccurate scope of work, etc.). 

We've been helping investors from Bigger Pockets buy in Boise where that rule does not necessarily work - that's because we try to educate them that its more important to take action on an pretty good investment property than waiting around for a "home-run" deal.