I then did my research over the next 24 hours and found more than a few red flags:Current Owner was in default on a 100% financing loan.A simple call to the Title Company revealed the offer was not yet approved.I then wrote him an email asking for the HOA bylaws, he could not produce them.

Benefits to invest in his business for some growth capital. new equipment purchase, and consolidation/restructuring of existing debt.I dont have any financial experience in regards to a business, and  just based on his explanation, something doesn't make sense with his income-debt(i dont know what exactly which is why i am here) My question is : " where is a good simple resource i can use to help me make sense of his books?"

I used Cozy, it's simple to use, and it offers pretty good expense report at the end of the year as long as your entries are accurate.

Also, a simple Google search should provide you with tons of companies. 

Does anyone have any thoughts or real world experience using company's like simple seg for online cost segregation analysis? 

Thought this might also benefit you.1st pillar is avoiding unnecessary and risky activities (don't drink and drive, insurance generally won’t cover your poor decisions) and take good care of your investments - these simple steps will help you prevent lawsuits before they even occur.2nd pillar is a good insurance policy as that cover the majority of your exposure.

@Josue Vargas I leave a new shower curtain and rings, felt pads for under the furniture legs, furnace filters and a brand new roll of toilet paper on each holder.

He is giving me the money as a loan at 13% simple annual interest.

Pretty simple.

The 1 in 50 times where this simple litmus test gets it wrong isn't worth the time suck represented by the other 49 times.Those that WILL drive to your office even though you previously didn't sense any motivation, it is probably worth your time to run a full CMA, offer them coffee, and start that relationship.