I appreciate any suggestion or concerns to further investigate 

I think I finally have an idea on  which company I will use for the purchase but  I could easily be informed to try something else or at least investigate it.

I've contacted Cozy customer support explained situation and requested freeze and investigation before turning money back over to tenant.  

You may want to consider what his reaction might be once he processes that the preliminary advice you've given him that he thought was in earnest, was actually for business solicitation because he might be taken aback by that.As for actual practical Tampa real estate advice, Tampa is unfortunately a really bad market for house hacking.

Several Turnkey providers I've been investigating recently are pretty aggressive at addressing deferred maintenance upfront, often opting to replace HVAC and roof which technically may have a few more years of life left.

My Question: I am completing my MBA and looking for jobs/preliminary career paths that can pay a solid salary while helping me learn the industry.

After investigation of the property there was quite of bit of neglected maintenance so the house was not suitable for rent and would not sell for what he still owed on the property.

I've done some preliminary searching but everything I have found has been more geared to building a home for the home owner and not from the investment side. 

Order a preliminary title report.

Is this something to investigate further or would you drop the mic and keep on looking for another deal?