I am about to buy my first property and with my detailed story I would love to hear what peoples advice on what to do in my situation to make the best of it.

Details: We've been looking at groves that are sub 20 acres, usually near 300-325k asking price, most properties currently have professional management on the groves, and almost all of the properties are without main living structures. 

In the scenario of the HOA being able to address the issues successfully by raising dues and special assessments, I could at least take a tax deduction for them.

For example: if the gain you are deferring would be classified as a short-term capital gain on that year's tax return, then when the deferral period ends (when you sell your investment in the QOF) any gain that should be recognized would be classified as a short-term capital gain.This is not meant to be a comprehensive list of all the details, but just a small summary of some of the main points I identified during my first read through the proposed regulations.I hope this is helpful!

Also, this will give you an opportunity to address deferred maintenance.

I am getting more comfortable with speaking to these individuals over the phone the more I do it and even meeting up with people for coffee to talk in more detail. 

You don't want to niggle over every last detail with excessive back and forth negotiating.

I had TD forward me the paperwork that was submitted to them and as it turns out, it was one page with the entire amount requested in cash hand written in (I had typed in everything on their provided form in exact detail). 

@Ian Boyle it's hard to know without more detailed numbers.

@Owen Dashner thank you so much for such a detailed and thorough answer!