Lessons learned: 1) Do a more thorough tour of house before purchasing 2) Have more money saved Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

With the obvious downside that it is a more risky approach, especially if you are not familiar with remodeling, design, appraisals, remodel costs, holding costs etc. 

But if you to a more wise and slow approach, you can find other ways to generate additional income, build up a 25% DP on a duplex that cash flows after all expenses and you have an EF fund, well you will sleep better at night and the odds that your investment will survive the tough times in your life is far greater then someone who sleep well at night with tons of debt who if anything should go wrong, which it does in life that person may be bankrupt. 

My primary goal with this initial investment property is to reduce my expenses by moving to a more affordable area where my PITI is less than my current rent.

Hey @Donald Muschany, I see you're in Sarasota - are you intending to have a more SW Florida (Cape Coral, Ft Myers, Naples) or more around the Sarasota area?

You can reach out to me to have a chat, or attend any local meetups that happen in the city (I also host one every month) to get a more realistic understanding of what the market landscape is like rn. 

That’s definitely the ideal scenario that I was concocting in my head to convince myself to give them a shot, but without them showing much interest in submitting a more formal application I opted to deny the request.

That will likely be a more accurate time.It sounds like you are a planner, which is why you are wanting to ask so far in advanced.

I suspect a more creative person than me could expand this list.  

A brand new building with commercial space on the first floor could mean new restaurants, shops, and businesses for the neighborhood, all of which would mean the area would become a more desirable area to live, and your property price would likely benefit as a result.