@Chris Baxter @Roy Cleeves @Tyler StillerThank you all so much for the encouraging feedback.

I am in a similar position as you, I’m 19 and not receiving BAH, but I will be closing on my first deal (a 5bdr SFH) in less than 2 weeks (knock on wood) if you have a lot in reserves, find a house hack where you live for free and possibly Cashflow and are committed to growing as a real estate investor I don’t see why you can’t use your VA loan and to get into another property.

Hi, A structural engineer will definitely help, the evidence of a fire in the attic is not an issue unless the wood is brittle, now those repairs in the foundation could be the issues to your cracks. the supporting post are ok.

@Roy Assaf, looking forward hearing more about your success!

He also owns properties in your neck of the woods. 

Louis, the Cultural Resources Office will make you put in historic looking wood windows that can cost $800-1,500 each vs. vinyl at $400. 

Louis in the south city area, everything is old so there isn't much to really set your-self apart and the 2 bed up the street will rent for the same price as the one your in no matter if it has a painted wood stair and newer front door vs. the stained wood stair and original front door. 

Knock on wood but I've only had to evict one tenant!

I don't have great photos yet, the wood floors are getting refinished in a few days then I will be painting.

Needed new kitchen cabinets, replacing a little rotten wood, landscaping, new carpet in Bedrooms and a few walls knocked down.