I am challenged by your courage to give up security and dive head first into real estate.I could totally relate to your dad saying, "not to trade security for uncertainty".That is the mantra of typical Asian parents, especially 1st generation immigrants.  

Getting started in real estate investing with an owner occupy multi-family is a smart way to go if you can generate decent cash flow.I would suggest that you start attending the local REIAs, Both Rarebird and North West REIA boast a group of really knowledgeable investors and it will give you a chance to network and learn about the industry.

Here're the risks:- Risk to buyer: Closing agent found out title not clean - transaction canceled. 

Is it to generate a phone call or draw out motivation?  

If not, is there somewhere in the leases that charges CAM's: landscaping, plowing (if needed), or cleaning the parking lot?  

Per old lease tenant moved in early received 4 days of free rent in return for cleaning.

Was cleaning out a new investment property...and found several boxes shoved under the stairs. 

So in your example, if you purchase the property at 320k can you generate at least $3,200 in rent?

A lot of people use Adwords and craigslist to generate and drive "instant" traffic to the site.

I wouldn't take possession until they are all out and the house is cleaned and spotless.