Buying a primary residence is very different than an investment property.

By no means is this an exhausted list. 

Annual contributions are 10x higher than an IRA and the plan has Roth and traditional built in.  

If you don't you're more of a burden than an asset.  

I would rather buy a great three unit than an over priced four unit. 

Any thoughts on whether this is more of a gamble than an investment would be much appreciated. 

The problem is that a small kitchen costs alot less than an large kitchen, same with the bathroom.

I'm trying to help out other CA investors (I still think buying locally is better than an inexpensive property OOS where you can't check up on the property)I don't know the Peninsula well but expensive Palo Alto, Los Gatos, Cupertino would be Class A to me.

Maybe, maybe notYou have to weight the pros / cons along with the risks.Your BP mentions you are 'new to real estate'.You are getting into a new asset class along with a business(I consider a STR more of a business than an investment).How much will you save in taxes?

Rental houses in your own name will be harder than an owner occupied house, but you may find a HELOC or fixed rate line at a local community bank, a credit union.