So, Will NOT selling the house now prevent me from buying a investment property in the future?  

They say I will make mistakes that they can help prevent but I am afraid that spending $30k on a bus tour is my biggest mistake.

Lastly, there are no laws outside of the HOA preventing more than 20% rentals; that is some sort of HOA rule and the owners ARE the HOA.

Yea no complaints but I like to be proactive and be preventive since it is the only property I own. lol kind of easy to manage since it has my full attention.  

You can record a memo of your contract, creating a "cloud" that may prevent him from selling.  

Like, if you are a debt collector talking with them about a debt and they are in bankruptcy, then you would be prohibited from speaking with them on any debt related topic.Also, if you are subject to any local or state rules regarding foreclosure prevention companies soliciting borrowers, you might want to read up.

However, lenders have brought to light that state laws prevent them from charging me what they would need to charge me in order to finance this as an investment mortgage.Purchasing it with a conventional mortgage as my primary residence would work (I don't currently own any other property), it is not what I am trying to do here.

Kevin,I've looked for multifamily properties on the MLS on and off for two years while we saved up our initial investment capital, but I've never seen one posted that was in "beginner's shape", so to speak; always large issues with the properties that would either require more starting capital to repair than we have or will be able to leverage, or otherwise have issues that prevent conventional financing.  

Is there some gov regulation preventing it?

My thought about having separate lease agreements (Bedroom A, plus use of common areas, and Bedroom B, plus use of common areas) was to prevent my son from being liable for his housemate's rent.