While I am not a fan of entering into a deal then backing out and suing, some of your claims need investigating. 

How can I better investigate this?

It may all be manageable depending on your willingness to investigate and then your willingness to tackle the problems.Your response to the inspection will depend on if you’re all cash or not.  

When I investigated that with the property management company, the president of the company claimed that when they first took over management of the property there was about $500k in debt and over the years they’ve slowly been crawling out of debt, and that $86k is actually really amazing considering where they came from.

A lot of them will be discovered when you conduct a more in depth investigation and during the due diligence process.I will provide a response to each of the 15 items you listed.  

What you’re proposing is something I need to investigate and make sure I build toward regardless, taking into account any requirements like dividing wall rules, placement of utilities, etc.Any chance you know if there are property tax benefits to keeping them together?

Since Jan 1, there have been 9 shooting homicides (pretty much all gang related), 15+ shootings (most appear to be gang related from initial investigations), and a bunch of car thefts (had a recent one month stretch that had 25 thefts).I'm sure this will affect the local market a but as potential buyers would see this and be turned off right?

Florida has some good STR areas though, It's worth investigating as @Jaron Walling said.

this case has gone to full investigation ""530 Center Street NE, Suite 100, Salem, OR 97301State of Oregon - Real Estate AgencyFrances Hlawatsch | Financial InvestigatorBest regards,Thank you again for the information, if I have further questions for you during the investigation I will certainly reach out.The Agency is well aware that unlicensed “wholesalers” are rampant in our jurisdiction.

Hi all, I'm investigating the possibility of converting a former big box store to self storage and I'm wondering if there are any basic rules of thumb to determine how much of a buildings space can be converted to storage vs the space used for reception areas utilities, hallways, etc.