Different approaches?

Approaching 50yrs old so clocks ticking and I can’t believe it took me this long to open my eyes to REI.

The key is to approach it as a conversation given you don't want to lose them.

Should I wait it out until the monsoon season is approaching? 

Will's advice is invaluable - I highly suggest approaching different agents with an "interview" mentality, but I'm always available if you have any questions about the DFW market specifically.Also, check out some of the BP calculators if you haven't already.

I’ll try that approach.

My plan originally was to always buy and hold for 5-7 years as i move through out my career but the crazy thing is the markets have always BOOMED as we approached moving time. it made more sense to me to cash out at those time than to hold the properties long-term with my living situation changing every 3-4 years. 

Make sure to approach it as a rental and not a flip.

How should I approach the seller(direct mail or hire agent)?

Your advise of backwards planning or reverse engineering is an excellent approach that becomes even more effective when identifying risks and mitigating those with various controls.