It actually can also be fun to have someone to answer to (like a wife and/or kids) and someone who you can share your adventures with. 

I called several of his references, and they had nothing but positive comments on the guy.We decided to take the gamble and negotiate a contract with the guy.

The only possible cash flow strategy I can think of is to gamble on rent control cities by buying out tenants to make the numbers work (much harder in SF now).

The only way for you to truly make money on this property is through appreciation, which is essentially gambling, but a lot more work. 

Let the adventures begin!

It's a gamble I suppose however these types of tenants can be big problems.

I believe there are plenty of careers that provide high levels of personal satisfaction and are not part of the so-called rat race.If you find yourself in 'job hell' there are several avenues out, none of which involve gambling your time and money on building a business which statistics say will probably fail.Living below your means is a tried and true method of building wealth.

With that I will stay away from trying to catch smoke and label "whats best" and instead keep to the simple of pointing out some poisonous ones.The 1st simple on is yes, you NEED an entity of some kind, doing business without a company structure of some kind is literally gambling with everything you have ever amassed because it is all available for the taking.

Sounds like you are just beginning your real estate adventures - otherwise, I apologize for some basic points.  

To help lessen the extreme and discomfort in my early twentys and thirties, I did Dale Carnaige, Toastmasters, joined various business groups and served on committes, did " firewalking" and a host of "self improvement" adventures, did bungee jumping, scuba diving and some other interesting things to become more comfortable being uncomfortable... or as jeffers admonished, feel the fear and do it anyways.