You will get tough skin, and if you can handle sec 8 you can pretty much handle any other tenant. 100k unfortunately won't get you too far in many places; BRRRR is fine but unlikely to pull out 100% of your money.

Originally I had planned to get the required permits from the city, but I had a contractor that I work with recommend to not go through the time, money, and headache of the permitting process since it's my primary residence and I can most likely "get away" with it.

Basically, stop wasting your time pining over a house that you sold and got money for and take your money and buy something else and make it better.Emotional attachment to real estate is a money pit every time.

I owe 400k on the house, so about 300k worth of equity just sitting there.1.I can get a HELOC and use the money for BRRRR, the problem is, I can't find anyone that is giving out loans for investment properties, I have tried most banks, up to PenFed, nothing so far.2.

This brings flow back down to 2700/mth with zero money in and 13 mths time. 

Another consideration for you since you are located in VA is the licensure requirements for private money lending.

There is major money involved in the right answer that impacts not only monthly cash flow but the overall value of the building.

I am planning on being married in the next year and a half and my partner and I are currently saving up money so that we can start investing in real estate, we are targeting fall of next year to start and should be able to have $80,000-$85,000 to invest.

There could be tax benefits in waiting a few years for the bulk of the money.

Will there be money left over?