Using Tools Like BiggerPockets:BiggerPockets has great "premium" calculators, but if you're comfortable with spreadsheets, you can create your own analysis template.

In my experience, allowing these professionals to guide you can be highly beneficial, as they are likely to recommend properties they would be comfortable managing.

Once I get to a point that it is making enough per month that I feel comfortable taking money out of the business that would be when I get to the point that it is worth have a specialist assist me in all deductions, credits, and future items that will help me to transfer from a W2 to working for myself fully.

Are you comfortable analyzing ARVs, purchase price, 70% rule, rehab costs, holding costs, etc

Yes I still have a somewhat high earning w2 income and I will be comfortable.

You can grow that account to what ever you are comfortable with.  

There are a lot of ways to crash and burn, so increasing the odds of succeeding long term should be your highest priority. you can always sell your local assets once you're comfortable managing rentals and ready for a market that better-suits your criteria. btw, kudos for being self-aware of your limitations.

Society and demographics favor smaller units since marriage and child bearing are being delayed.  

The high HOA fee is already a factor, so ensure you’re comfortable with the overall carrying costs.Focus on the Land Value: Since the lot has development potential, you’re looking at this as a long-term investment.

They are too close for comfortable game play.