I've got a few suggestions here:
1. Worry first and most about liability coverage. That is where your true financial risk lies and where I want to see you professionally covered. Not in physical damage. That's peanuts when compared to a liability lawsuit. For those who aren't comfortable with insurance lingo, liability covers what or whom you hit and the $ amount of damage caused when it happens. Large liability losses were what I insured for over 40 years.
Please let me repeat: A liability suit can wreck you financially. A physical damage loss will never send you to the poorhouse. You want a liability insurer whose name you recognize...Liberty Mutual, Hartford, Aetna, GEICO, USAA...somebody like that. They'll defend you the way you deserve to be represented, they've been in business a very long time and they get taken seriously in a court of law. Nobody pushes them around. Buy coverage from Lloyds of Laredo or Shifting Sands Mutual or any insurance company whose name you don't recognize and in a courtroom you could be holding a very weak hand. You truly get what you pay for everytime.
2. Get at least a limit of $300,000 to $500,000 on your primary auto liability policy and then purchase an umbrella policy to protect you from large bodily injury and property damage losses under your homeowners coverage, automobile liability plus other things like personal injury (which will involve damage to somebody's mind, state of mind, state of well-being, slander, libel, defamation, damage to character...anything like that). If possible purchase the umbrella coverage from the same company who insures your automobile liability and homeowner's coverage. Buy a limit of at least $2,000,000 and preferably more. It isn't expensive. The more the insurance company has to lose, the harder they'll fight because they don't like losing their money.
3. You do realize Hagerty is not an insurance company, right? They're good people and they know their business but they're just a commission paid agent.
4. Here is a really important point and if you ignore everything I've said up to this point that's fine. What I'm going to tell you now is incredibly important to you and your family and should not be ignored by anyone. Insure your house and please if possible over-insure it. Talk to your agent. Look him/her straight in the eyes and make completely certain he understands you want to buy a policy which will pay to rebuild your house exactly as it is today using the same quality of materials. The fact is two thirds of homes in the USA are under-insured by anywhere from 25% to 60%. No kidding.
You may have seen on the news there were serious fires in Ruidoso, New Mexico lately. Around 1500 homes and other structures were completely destroyed. Many people there are now realizing they don't have enough home insurance coverage to pay to rebuild their place. And some of them will be forced to either leave or live in a much smaller house or take out a loan to rebuild. Construction cost there is estimated to be around $285 per square foot. Some of these folks could not pay to build 1/2 of the house that just burned with the funds they're going to receive from their insurance company. Please don't let that happen to you. I realize it doesn't concern old trucks but it could be heartbreaking, it could disadvantage your family terribly and it is so easy to avoid this.
