Consider closing in person using a cashier's check if possible. 

IMO, if you want to leave your day job, your investments need to be high-cashflow. i would personally sell anything that's not giving you at least a 10-15% return on your equity, and 1031 into something that will be a little diversified but heavy on cashflow, like a 3-4 unit multifamily in a great STR and MTR market, using a few units for each of those two strategies. you can do this long distance easily & would 100% meet RE PRO status if you're self-managing a STR unit (double check with your CPA as everyone's situation is unique - this is not tax or legal advice). if you can buy a crappy one and BRRRR it, you could do this twice with the same startup capital from the 1031, and idk what your monthly cashflow goals are but that would put you in a pretty good position so long as you buy right!

Most anything within walking distance of the Battery, IMO no one is going to care about having or using a hot tub.

We believe we can build for 200k a unit (very inflated number, most likely lower but using a conservative estimate).

That is the standard list of documents required by all banks if you are using a traditional loan. 

I met a new investor, with contracting experience, at a local real estate meet up and he is interested in doing a flip using a hard money loan, renting the property out to his girlfriend, then using a FHA loan to buy it so he can live in it.

You already left a trail behind yourself that will lead to you, even if you start using a land trust, and, 2.

Matt, first thing to make sure is that when you are using a HELOC it is for a short-term loan.

I was looking into using a pre-approved/package home design thinking it would save me money but it would only save about $5k.

I would have to know the market to an extent that I believe my valuation is as accurate or more accurate than the appraiser's valuation for me to forgo an appraisal (in my market at one time I felt very confident of my valuations as I had actually seen the units that the appraiser was using as comps and had far more familiarity than the appraiser). forgoing the appraisal was a big mistake and resulted in you paying way too much for the property.