I bought my second property in 2013 with the intention of living in it for a year and renting it out, however I met someone, fell in love, and that home turned into our personal residence, so I didn't get to rent it out.  

AAGLA Needs Your Help in Defeating AB 2819,a Bill that Hides a Tenant's Bad Behavior from Property Owners AB 2819 Bars Access of Owners to Critical InformationAbout Past Residencies, Failure to Pay Rent.Tell your legislator to VOTE NO on AB 2819.AB 2819 (Chiu) is another measure that ties the hands of rental property owners when a resident doesn't pay his or her rent.

But he seemed pretty sharp, and was even considering selling his personal residence up there because of how overheated/low affordability Marin is getting.

Many of the leases are MTM now and some residents have been there 2-5 years.

I though there was a requirement to hold a HUD property for one year as a primary residence? 

It is our personal residence. 

I don't know if I can answer them all but I do have something to add.I assume you are going to live in one half for a while at least before moving on and keeping both halfs as rentals.Consider the location and what type of resident will be renting from you, and being your neighbor.  

My guess is that to take a 3/2 and convert it for 10 residents, at the very least you'll need to be adding some extra bedrooms (and possible adding additional square footage).

Both my wife and I have VA loan benefits so we were able to turn former primary residences into rentals since we didn't need to free up the equity.

A resident manager fee?