Always great to hear from a fellow Texan.I might suggest to think about House Hacking as something a little different than "an investment".  

And if anyone has any suggestions on questions I should ask a tax strategist those are welcome as well! 

If you're looking for meetings I suggest checking out REINTN.org There's constant meetings on the schedule and you can attend as many as you want.

I agree with what @Caleb Brown and @Alec Barnes have suggested.

The tenant swore there was mold so we came out and found no visible mold however we did treat the surface areas with a spray product sold at Home Depot called "Concrobium" then we followed it up with treating the walls with Hydrogen peroxide. of course this was to ensure that the tenant could not say we were unresponsive which is also why we made a video while on site showing no mold.It was a relatively cheap way of responding and in the end the tenant later confessed that she simply needed to break her lease.

Curious what strategies are out there and some suggestions on my next move, any advice is appreciative. 

If it holds at the current assessment showing on their site, at $600 it’s doable.I’ll call the city Monday morning and find out when the final assessments will be released.Thank you so much for pointing this out!

For the second house, I would suggest having additional 5k because you can now spread out the risk over 2 properties and it is unlikely that 2 AC units go out at the same time or that you have 2 tenants trash both properties the same month.  

what is best software to find unpublished land on RE sites?

I would suggest taking a weekend with you and your wife and plan out the next 3-5 years.