Regarding a downturn in the market, we look at the data very closely and I'm not seeing anything on the horizon that is worrying me.

If I were earlier in my investment horizon, I would be very leveraged to the extent that the numbers worked.One dimension (there are many of course) of an unleveraged property I consider is the comparison of the net income they produce to the "yield" metric that a securities position would deliver if I instead used that cash to buy stocks in my brokerage account. 

Sounds like a good deal...are you sure there are no back HOA dues that you would be responsible for...and @Stacey M. has a good point about any assessments on the horizon 

Later on in your career I absolutely recommend broadening your horizons and branching out to other areas of investment deals, but to start with, try to focus all your efforts towards one area of real estate.

My goals are specific to retirement needs and I have a 15 year horizon.

He looks to be in his 50's so your time horizon may be different.

Need to expand horizons.

Wesley Chapel may be "booming" today and you have to be aware enough to see any trouble brewing on the Economic Horizon. 

You had the perfect storm in 2006, stopping you from making money out of RE.Many will point to a SIMILAR storm now on the horizon - and NOW you choose to go again?

I would get out and talk to full time real estate professionals and inquire about shadowing them and possibly interning with them if you see something that really interests you.It will broaden your horizons and let you see what all makes up the real estate industry.The more people you talk to the better off you'll be.