I can throw out some general numbers for you, knowing that it will depend on a variety of factors for your individual situation.

I live in the Hartford area of CT and up until learning about the BRRRR strategy on BP, have really only been focused on an owner occupied Multifamily (3 or 4 units) as I was pre-approved for 5% down up to 275k (more when 75% of property income factored).

You need to factor for property management.The goal is good, just make sure the math works.

I can tell that you are a numbers guy.I would encourage you to spend a few minutes with every deal working on your gut-check factor. 

Properties in high crime areas aren't worth much so you can't buy them for the appreciation factor.

Now that I think of it, another limiting factor to this would be the veterans DTI, correct?

When using the wholesale equation: Max Offer = (ARV*75%) - Repairs, should I also factor in holding costs, transfer costs, closing costs, marketing Ect?

I understand that capital, experience, net worth, and liquidity are all factors for securing investors and financing.

So shouldn't the total ROI be somewhere in the results factoring in the built in equity at purchase of $40K?

That needs to be factored in with the amount of consideration given for the option by the TB.Whether you stay on and manage it as a rental or not depends on whether you are assigning or sandwiching.