Everything about building Accessory Dwelling Units in Ventura1. 

@Michael C Williams is correct in that many places in San Francisco convert the ground level garage and storage areas into legal dwelling spaces (ADUs), but IMHO these are not the best properties to hold long term as it changes the classification of a property from a SFH to a multi unit.

Most companies that insure multi-family dwelling in Personal Lines use 4 units at the cut off.  1-4 family are eligible and 5+ need to go to Commercial lines. 

www.homeadvisor.com and www.angieslist.com are good sources for contractors and both sites offer feedback from the public on the contractor's performance.That and I would terminate the PM company instantly and make sure that they don't have access to another cent of your money.Good luck!

I can't find any 5-bed resale homes in our market for anywhere close to that price, so he likely has some instant equity. 

Below are 2 quotes I received: 1) $1,723/yr for 300k liability, 225k dwelling with $2,500 deductible2) $1,982/yr for 500k liability, 267k dwelling with $1,000 deductibleI'm thinking to do $2,500 deductible for lower monthly payment but unsure about how much liability coverage I would need and should get. 

If we did the latter we could buy it as as our primary dwelling and get better financing for it.We're still trying to figure things out on that.

As long as the home office is within the dwelling unit you don't have to prorate gain between excludable and non-excludable. 

@Mike Hinkley with this property in the grey area of Single or Duplex, any agent will need the underwriter to get involved and provide the proper policy forms to make sure you are covered for the unique set up.Normally, this location will be your primary home, and you are buying in your individual name, the only option you will have is to insure it as a Homeowners policy, by definition is a policy for an "Owner Occupied Dwelling".  

The bathrooms need renovations (one worse than the others), kitchen could use a facelift and some new floors would instantly raise the value.