The first hurdle was finding a warrantable condo, which proved to be a daunting task despite exploring over 20 different units.

But here's some tactics to explore and compare.1.

@Vinay M.Recommend exploring as many sources as possible to get referrals AND cross-reference them to get as much accurate information as possible.Check out NARPM.com, BP’s Property Manager Finder, etc.Also, encourage you to learn from the mistakes of others - by reading posts here on BiggerPockets about owners not having their expectations met by their current Property Management Company.

We are exploring the idea of renting it.

@Sonya Gulka I live and invest in the metroplex, there are a number of great areas around here to explore. 

DM me if you want help or need to explore more.

4) Model Scenarios to Explore Opportunities - WHAT IF scenarios!

I would recommend exploring Orlando and the West coast.

Additionally, you might want to explore reaching out to your local Investors Group or BNI Group for recommendations.

Home insurance is not designed or priced to replace roofs every 5-10 years and then to double down and say that doing so doesn't affect pricing is just nonsense.The roofing practices you mentioned end up getting legislated out of existence (see Florida) because they're untenable.I agree the original poster should explore every avenue but there's no way a legit roofing company is going to be able to "turn this around on the insurance company" in this scenario.