Do you pass up that property because it's to much of a gamble?

Personally, that's too much of a gamble to take.

San Francisco, Hawaii, Los Angeles, Seattle, Boston are examples of primary markets which are NOT ideal for cashflow investing.It could appreciate but I consider that gambling.

Could be a different neighborhood in 4 years and you got in early but has to be a gamble your willing to take.https://www.cityofrochester.gov/BullsHeadRevitalization/

When we invest in real estate we take a higher gamble than most at being a target for litigation. 

Many officers in ft Benning go to the captain career course on a 9 month PCS and end up staying for 6 years so never assume you are fraudulent on any action of where you will be at the end of the year because no one can tell you the military's next move in your career. 

I do not think his money comes from fraudulent sources and he does not even speak to me about asking for a loan, rather he told me to buy in cash so I can supplement the rest of the payment.I know he has paid his taxes since he is here and he has an ITIN number with the registration of those taxes.

Banking on appreciation is just gambling. 

Banking on appreciation is always a gamble, but it could potentially pay off in the long run.You might consider putting in a lower offer.

They do it illegally... it's a gamble, especially because the heights has some very nosy neighbors and the city has apps that make it exceptionally easy to report these things with a few clicks.