I spent 40+ years in an interesting niche of the insurance business. GEICO, Hartford, State Farm, Progressive or whoever you're comfortable with will be just fine and in a moment I'll tell you about another one. All those companies are very good on liability claims and those are the claims that take you to the courtroom. I don't purchase physical damage (collision, comprehensive, etc). I could tell you more about why, but it sounds like you just want liability coverage. By the way, Hagerty is just an agency...not a company. Not saying anything bad about them...I think they do a fine job at what they do, but some folks seem confused and seem to think of them as an insurance company. I said I'd mention a company known for good claims work. I give very high marks to American Modern Insurance Company. Those folks still operate like insurance companies did 50 years ago and they're as strong financially as they can be. A+ rating from AM Bests, and there isn't a rating higher than that.
Also, if I want to drive my pickup every day of the week, if I want to drive 25,000 or more miles a year or drive from here to Canada, I don't want any limitations in my coverage at all. Almost every insurance company will offer you a lower rate if you agree to drive 6000 miles or less per year and if you have multiple vehicles. Good luck on this. Personally I'd call the agent who handles my other personal lines (homeowners, auto, etc) and see what he/she can offer you. See if that agent represents American Modern if you're curious. I promise you they won't blanch if you ask them to insure your 49 pickup. They do that all the time.
