There are other riskier assets that I think should go up but they are far more of a gamble so I am using our retirement money for those.

To me, it is speculation or gambling.

I considered using him, but his online presence is really poor, which means unfortunately I'm not going to take a gamble with a huge investment, on him.

It would simply be one big spam fest if that were allowed, which is why its not.  

I guess the main reasons I’d want to keep the house are 1) ego - to be able to say “I own a rental property” and 2) hope for things to magically turn around and one day sell for profit (gambling...)What would you do in my shoes?

The office confirmed with the owner that 66% of the balance due was a good gamble and we took the money.

However, we quickly learned that these prepaid phones get TONS of spam calls and we have decided not to renew the contract when it runs out.

If you do an auction, you just have to be okay with the gamble that you might be buying a lemon with a ton of problems!

Hence, you're asking for gambling advice from someone on the internet. 

These markets also have a great employment rate with large companies such as Procter and Gamble and The Kroger Company - together employing over 33,000 people.