My partner and I were stuck in the analysis paralysis stage for a year before we pulled the trigger on anything.

Would you fellow investors pull the trigger on a deal like this or pass. 

I looked at so many properties scared to pull the trigger but finally did when I saw this one!

In Cook County, IL, my understanding is you may or may not trigger a property tax reassessment based on a sale and otherwise it’s somewhat unpredictable when an actual human will come to reassess the exterior and interior for overall value.

Cash is NOT a qualifying asset, though, so if you receive significant refi proceeds and aren't able to redeploy them before those end of June/December testing dates, you could fall short of that 90% asset test which would trigger some fund-level penalties.

I’m not ready to make another purchase yet as I want to get this current deal going, but I’d like to find a reputable lender so when I’m ready we can confidently pull the trigger.

Get with your CPA to calculate the tax implications before pulling the trigger.  

I am very eager to learn and start out and ive gone as far as finding a private money lender that is ready to pull the trigger with a remodel, and I have a couple of handy men ready to work as well. 

WIll this trigger massive selloff in Texas?

The two issues to ask about are whether this could be treated as passive income vs. active income, and whether ongoing losses would trigger problems.