I gained equity in the property, and I got higher rents which lowered my living expenses while living there.

I have been fortunate to meet two of those individuals and gained a mentor.

Both @Nathan Gesner and @Lauren Stark have provided valuable insights on this.One potential path for you is to join an established team to gain experience.

If anything, at least wait a year so you don't pay short-term capital gains on the sale of the property.I need to find some more deals like that here in Chicago...where in Houston was this property?

No reason for me to go the through the hassle of the sale process unless there is some type of gain which the investor is open to and this is where I need the advice.

It's low risk and tax free on the gain.

If I can park the 388k ($415-27k) for one year at CD rate of 4.5% and then est 300k (after paying cap gain/depr recap) at 3.0% (assume CD rates lower) that interest income of about 24 months net of ordinary income tax is about the same as my current mortgage.Trying to play devil's advocate and think why selling this year does not make sense. 

If you have lived in it for 2 yrs I would suggest renting it for 2 - 3 years and then selling it to avoid capital gains taxes. 

I am planning to get into the TN real estate market as my first investment and am looking for some information.In particular: Areas to steer clear of, property management fees, typical cosmetic rehab costs, etc.My strategy is to put large down payments on 2 properties (relative to housing prices) to help pay for my living in NY while still gaining appreciation in a growing real estate market.

Your development deal will look much like a flip in the eyes of the IRS since it is 6-9 months as well you'll have the short-term side of taxes, not the capital gains taxing on it.