Any advice or insights would be appreciated.

Oregon were i am at is bad with this as well on the resi side.. but on Commercial there is no squatting those laws that resi tenants have do not exist for Commercial you post a 3 day notice and then you can legally enter change the locks kick whoever is in out.. that includes your commercial tenant that is not paying. 

There are a lot of people not in just my market that have stated the change in the market for rents is extreme to some saying it's minor.

We also want to stay in a nice price range of $1,800-$2,200 as going above that changes our competition.

Does anyone have any insight on whether other insurance companies will insure with cloth wiring or companies that offer good coverage?

(Not really a surprise that CA makes life a little harder)The California Franchise Tax Board will require that you file a new form every single year (Form 3840) in which you detail what you did with your sale proceeds, where they are invested, and whether you ever recognized income from your sale or any subsequent sale.  

My current agent advised me not to "rock the boat" with the policies I currently have because they are all older and would "go up significantly" if I changed anything.

I have no insight into the Maryland market but you're doing the right thing by consulting with experts on here.

One thing I think would be interesting for the Bay Area (and other major cities) would be identifying which areas with bad school ratings are seeing a demographic changes.

What this means for you is that this is the amount of time that your capital would be invested in the deal.A hold time of around five years is beneficial for a few reasons:Plenty can change in just five years.