In your shoes  (if you wish to proceed) I'd push to have the eviction completed prior to close as a contingency.I applaud your interest in getting into real estate it has been a very rewarding and enjoyable career for me.

The right deals are rewarding ;)

It is very rewarding!

NOW, if we are to have the HOA responsible for the interior of each of the units as well, here are the eminent problems I foresee:    - owners will be even more careless and act irresponsibly for their units since they don't pay for the repairs of the interior of their units    - because many of the owners rent their units (technically they sublease), they will be even less incentivized to maintain their units    - the HOA pays for all maintenance and repairs of units and owners get the benefit of rent    - repairs/maintenance of units is not properly proportioned to their respective owners, meaning that there is no incentive to keep my property up because any repairs will come out of the pocket of all other owners    - this penalizes good owners and rewards slummy owners    - this will put the owner residents at a big disadvantage because the owners who rent their units will cause maintenance fees to increase for all owners, especially due to high turnover    --> in Summary, this is a straight example of socialist-style system (I know, my family immigrated to the US from the USSR) and it will just sink our whole Co-op.  

I want to keep him enticed/rewarded enough to stay involved down the line but want to make sure I don't over-promise and stall my future plans. 

How much more risk/reward compared to San Diego? 

Amanda,Yes, I think that individual's like yourself who are tenacious, self driven, and hard working should open their mind to all the opportunities (not just real estate) that exist where their drive can result in rewarding and profitable work.  

Multif family is bigger game with more risk & rewards.

Some people love the sandwich deal, but be prepared to potentially deal with headaches, because they do happen every once in a while.At the end of the day, which strategy you go with is entirely dependent on how much risk you're willing to tolerate, and whether or not the potential reward justifies the risk.

Flipping is more exciting and rewarding for me because I have a chance to create something beautiful from something ugly each time.