Here are a few pros/cons off the top of my head:Pros:Buying in Sonoma coast area:  Strong vacation rental market relative to price in some areasExisting services for marketing and maintaining a vacation rental propertyProp 13 will keep your taxes lower for the long haul (as you noted)It's where you want to be and end up, so whether or not it's a great cashflow or appreciation investment, it will be valuable to you.Buying in Bay Area:It's where you live.It might be cheaper than rent,If you buy at a fixed rate, the future affordability more assured in 10 or 20 years than rent, assuming that both rent and home values go up as they historically have.It will likely cashflow like gangbusters if and when you decide to move to Sonoma for retirement.At retirement, you're likely (historically) to have equity that you can pull for a future Sonoma purchase as well as cashflow from the home if you hold it and rent it.Lower interest rates, more loan products (i.e.

Aren't there companies that I can designate to hold the rental monies to assure the taxes, WSG,  Insurance & the  monthly payment to me is automatically paid.  

I assure you VA did not know or authorize this to happen nor did the Asset Manager   Unfortunately VA, HUD , Banks or even an individual who forecloses on a property has no duty of disclosure in most statesHopefully it is just household items and trash and all will be ok.

@Brock WibergSomething is rotten in the state of DenmarkYou cannot contractually remove a right that is afforded/assured under law.  

If you want to assure yourself of being audited, I'd say do your taxes yourself. 

They ask for for my info and the more senior of the two provides me with a business card, a firm handshake and assurance that they would be following up with me promptly.

The first thing we did, @Jason Turo , was to find the worst real estate attorney on the face of the earth who assured us the note and deed of trust we obtained from our first borrower was sound.

Under this program you  will be  assured, you and your buyer will get approved if  there isn't  any problem in appraisal.

You have a house burn down and kill a tenant due to unpermitted work and rest assured you'll be spending a lot of time in a courtroom.Now, can you rent rooms and then put certain areas off limits?

I own both older and newer rentals but I assure you the increase in rent is much higher on the newer properties.