It's just the way it is. I'm in Mass like SeaJay. I have a million dollar policy and 30k garage keepers policy. It was like $860 a year and had to be paid all at once.
Garage keepers is for damage to the car. I could be working on a $75,000 car, if I back it into a wall I'm not going to cause $75,000 damage. The damage would probably be a few grand to fix.
It is my understanding that you do need the 1 million dollar policy to work on any commercial property. That includes dealerships, parking garages or office complexes. I don't bother with any of these even thou I have the coverage.
My policy also has a waiver for the other services I do on RVs. Winterizing RVs and rubber roof treatments.
As far as the commercial plates. I also had to do that. In Mass as soon as you put lettering on your truck it becomes a commercial vehicle and needs proper plates.
If you a sole proprietor and have no employes I don't believe you need workers comp.
I spent the up front money to do everything the right way. If I didn't what would set me apart from the guys on Craigslist doing the $50 details?