Yeah he is old school, but he’s done well for himself sticking to his gut feelings.

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.

When we bought ours we had to kick out all kinds of problem tenants, but we remodeled them nicely and are very strict on the type of tenants we allow so everyone feels safe and comfortable living there.

Some new tenants are very good at talking and making you feel good so they get the property. 

What are you feeling you are lacking to take the next step?  

Do you feel like there is a housing shortage at all in Lubbock?

So I really feel like it could appraise for $625k after closing the first leg and trying to do a refi.

If you feel more comfortable having a lawyer review it, that is still a stronger starting point to save money since they are not starting fresh. 

Looking for advice on raising about $1.2M quickly (2 weeks) from my existing network of doctors. 

If you would ever like to meet for coffee, feel free to reach out any time!