If you're a car guy it's like Jay Leno telling you not to buy a classic car until you can afford to pay to have a total restoration done on it.

Attorney by training, co-manage a credit repair and restoration company, plus income-producing real estate (just started that in the past year). 

I'd put in 15k or so plus six months of sweat, blood, whatever it took to restore some rock solid mid century beauty.

I use Bobby D at Integrity Restorations for work on my houses in NE Philly. 

My analysis paralysis is, should I try to brrrr and or house hack a sfh in my area (using hard money for the rest) or should I start investing out of state as my first investment?

One of the "depends" in "It depends" is where.One of the leaders of my investment group specializes in historic restorations.

Whichever way you decide to go, you have to make sure you have a Public Adjuster on your side, so they can be your advocate in getting the most from your claim, as well as a good restoration company that also does the rehab, so they can point out all the things needed to bring the property back to a habitable condition & the cost (the need for these ppl also applies, even if you're going to sell, since you'll need to know what the proceeds will be).

I was chatting with my roofing guy (who owns a Fire, Hail and Flood restoration company) about buying fire damaged properties, fixing them up and flipping them. 

Invest in deals and get high returns in 6-8 months.Look into buying or acquiring a Home restoration company that already exists and is doing well. 

You will have to apply for a "1-Time Restoration," however there are a couple other steps. 1 - you need to refinance both homes into conventional or some other financial product. 2 - you need to apply for a 1-Time Restoration through your mortgage broker.