My personal one also covers all of my vehicles, my boat and my primary residence.I use Strategic Insurance Service in Clearwater, maybe you can give them a call and see if you can get a better quote.

For out of state owners, when you're in town, meet with the neighbors, pass around your business card/contact info and let them know that they are to call you with any concerns - noise issues, trash violations, new dogs, too many vehicles, etc.  

Who really knows, but keep in mind that your "personal exposures", such as your vehicles, home, etc...

Again a good used vehicle can save money and remain reliable as long as you maintain it. 

Your credit already sucks and vehicle repo only matters to auto lenders just like foreclosures matter to mortgage companies.

Vehicle, fuel, GL insurance, state licenses, tools, etc.

You may luck out and find an asset, maybe he has extra vehicles like work trucks. 

I will point out though that the company owns my "personal" vehicle similar to what you described.

It's like driving a vehicle.

He broke into a storage building and smashed up my vehicle inside.