My end goal is to supplement and eventually replace the income from my day job.

I do want to transition into multi families and specialize in them eventually, but I'm wondering if it would be better to do another SFH prior to establish some kind of track record.  

They run specials for $199 for the class and materials on the coupon sites like Amazon deals and Living Social. 

At least in the areas I specialize in (top school districts) S.

You are opening up a whole can of worms and risk.And frankly, if I was a tenant and you put it in the lease that I was to show the property, and I felt contrary, I'd have the place trashed specially for viewings.The only time you can get tenants to show a property is if you have really good tenants who will work with you.

The Bay Area is a special place but you can do well here if you stick to your plan.

They might own multiple properties or receive a special discount having all insurance at the provider and your insurance rate is much higher for a single policy.Make sure not in a flood plain as those policies have gone way up in the last few years almost doubling or tripling.Many other things these are often overlooked.   

Scott The Book on Flipping Houses, The Book on Estimating ReHab Costs http://www.biggerpockets.com/flippingbookYou might consider Niche or Specialized Housing like student housing.

Hi Ben, intriguing idea and I can't answer most of your questions, but the one thing I will throw out at you is that this would likely be considered a commercial loan by most lenders (but not by all) and a lot of folks who specialize in those won't do owner-occupied projects, as the disclosure and regulatory requirements of each don't always jive together.

Scott The Book on Flipping Houses, The Book on Estimating ReHab Costs http://www.biggerpockets.com/flippingbookYou might consider Niche or Specialized Housing like student housing.