@Dillon DembowskiCongrats for taking the initiative so young - your goals are not too lofty at all.1.

My team and I walked away with some very valuable knowledge and experience, as well as doubled our initial monetary investment.

Well I think the good news is the refi from the deal itself is going to take its rental income into account for the DTI calculation, while DTI from the initial HELOC will not. 

My initial rent analysis for the area we prefer to invest in shows rents around $900k-$1400 for a 1/1 unit, depending on updates and size of unit. 

I'm looking at developing Area, smaller municipalities with some R-4 Rural (Duplex or Rural Comm) that could be used as a land split to get the initial investment money back rather than trying to force appreciate the home itself and simply Rent at a slight cash flow ($50-100/mnth, $150 is the best I've found on MLS)   There's obviously some serious risk here because the initial $500-$3000 for the application doesn't come back to you, and you could very well be denied depending on exactly what you buy then left with a cash-in property with low returns.

Very experienced investors or people with a lot of construction experience are sometimes comfortable doing their own “inspection” on the initial walkthrough.

I paid an initial 19K deposit (1/3 of the 56K total SoW).

I would not want a business owner renting from me also having an endless cost hanging over their business that brought no future value.You might want to limit your expense to initial primary lease term and not the options paying the leasing broker.

@Brian Koziel I thought florida had two options with a check box for what they agree to on the initial lease.

I am hooked up with a wholesaler as well as with a few agents and want to start making moves; I just want to make sure my initial step back into real estate is the right one.Looking forward to any and all feedback.Best regardsFreddy