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.

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.

You can even draft and include a personal guarantee as added assurance. 

It's not the new hard wood floods, marble counter tops, pool and Gazebo, That the only thing they don't make anymore, it's where the true value of real estate can be found, and why would any professional Realtor not tell their clients that a current land survey certified to them ( not some other dude ) and dated within the circumstances of their purchase is the only assurance that they have title to what they have agreed to buy.  

Your title company will probably ask for an updated letter testamentary to assure the Executor is still approved by the court. 

@Christopher Blanco I can assure you that there are many deals on the eastside on the MLS (especially at only a 10-20% profit on a flip).

Keep your chin up--I assure you, you can do it!

If conventional lending is your only source, and I assure you it is not, ask around at the smaller, local banks.

Any suggestions on other ways I can get the lender the assurance he's looking for without incurring this expense?

Yah Dave and I met; he seems competent, self-assured, and reasonable.