I've obviously allowed my idealism and view of what could be to get the best of me.

I mean don't get me wrong it wouldn't be ideal but worse case situation the math still worked.

What natural talents do you have that will make you well-suited to being a real estate investor? 

Hi Caleb,If President Trump follows suit (two card references in one sentence, that's pretty good), he will probably issue more cash in WORKERS hands on a weekly basis, and pull out the stops (a pipe organ reference) for Entrepreneurs and big businesses to create more jobs, as well as close down the amount of people coming into America looking either for a free cradle to grave handout, or seeking jobs Americans need.So I suspect we will experience a swift (as swift as can be) injection of more spendable money to the WORKERS, with continued care to the Cradle to Grave Welfare recipients, and less restrictions on business, because it worked very well when he took over.

Ideally, I would like to add a full bath and have my home appraised as a 3/2 and use the added cash-out towards my next home.

Leaving too much time on the table has a tendancy to sour a deal in my opinion, though it is ideal for you as an investor in uncertain times. 

There's no shame in getting it filled less than ideally to help prevent bleeding funds. 2.

(If so, you have to be grandfathered in under the old rules or be outside of a 500-foot radius of any other existing non-owner-occupied STR) Or are you talking about a basement apartment/mother-in-law suite in a primary residence?

Although not ideal, I think this is much better than forking out $500+ a month to rent somewhere vs. paying down my own home.

I realize that house-hacking is ideal because it gives you a place to live (and get your mortgage paid by the other renters), so if you can get a co-signer and go conventional, that's perfect.