The exit strategies that you can come up with will tell you if you are rushing, IMO. 

Taxes are $500 a month and insurance is $250 a month.

Define your retirement, time frame, then ask for an REI strategy to get you there.  

By the grace of God I've managed to hang on to most of my family's Farm from government aided land grabs and I'm looking to educate myself on the various options available to me for an exit strategy of this property.

The large scale BRRR can be tricky, but having a JV from the start will help.My clients down in GA are doing well with a BRRR centered strategy, but focused on one, or both of these things to cash flow quickly:1) 2-4 unit properties2) Section 8In most lending circles, your 2-4 units are going to be classified in the same category as a SFH, so to rehab a hand full of those, you don't take the same kind of rate hit as the 5+ unit properties, but you also don't have the same kind of "experience" issues as you do with larger developments.

His insurance company has denied his claim.

Pittsburgh is a good place to start, but the strategies vary depending on the area you are investing in. 

I think a lot of the decision about investment strategy - LT appreciation vs cashflow in this case - is as much about the investor's current position as it is about the market.

There are multiple options depending on your end goal, capital position, long term/short term strategy etc.. 

So a few points I want to clarify, FDIC insurance is for bank deposits and won't have anything to do with a credit card so don't worry about that terminology when you're searching.As far as building a relationship with a bank I would say it is more important if you don't have good credit and want favorable terms, in your case with good credit it shouldn't make a world of a difference.