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.

Morning @Ryan Daniel Palmer,Maybe Cash for keys, I'm sure there are tons of posts about it and how to approach the conversation.

With tax season approaching I’m looking for someone who can help with write offs and also future REI in the future.

I believe it is a short-sighted approach because times might change and demand as well as free cash might dry up and then all the long-term investors who understand the benefits of leverage will have moved to those TK providers who understand it systemically.It also begs the question if TK providers really have the best interest of the investor in mind as pushing for cash purchases removes one important accelerator of ROI.