Do you think after the 2020-2021 increase, there will be another increase on the horizon in the Round Rock area in the foreseeable future?

I definitely think you can hit your goal of getting $10K/month in net cashflow WAAAAY before your 20 year time horizon. 

When you look at the whole picture and seek to make big hairy audacious super-optimized moves with a very short time horizon it can very easily lead to paralysis.  

Using the equity would save about two years off of our purchase horizon.

Good stuff @Stephen Brown thanks for sharing...it's great to hear about a comeback on the horizon...I'm pulling for Dayton myself ;)

Myself and other smart people around me are seeing potential buying opportunities on the horizon. 

In your opinion, is it on the horizon where the county passes some form of STR regulation which impacts all cities?

Philips, Winter Garden, Horizon West, and Celebration. 

What most forget about JV's due to their focus on raising capital, flexibility, or broadening your investment horizon is that it is a partnership and if you think Real Estate investing my be stressful at times throw a few inexperienced partners in along with money they are looking at and having to work together as well as manage emotions and you have a perfect storm.The point I am trying to make is the successful JV's I see are comprised of experienced investors who have opened their financials to each other, as well as background checks or any other verification of finances and more importantly character to have a comfort level with one another.

Also note that the national builders would be more likely to buy an option on your parcel if you give them a longer horizon.