Hagerty insurance specializes in insuring older boats. Many insurers do not understand the intricacies of older boats and have underwriting guidelines/rules not amenable to older boats. Hagerty has been able to offer the flexibility and understanding to insure a sound vessel. They aren't the lowest priced insurer, but they will be able to
work with you in ways that other insurers can't or won't.
With respect to wanting to own an older boat because you feel it is more affordable... I feel that reasoning has the potential (especially for first time boat owners) to backfire and cost you more
money. I own a 1977 Bayliner Victoria. By many standards (especially among Bayliners), the boat is considered a
classic. I purchased it with the intent of restoring it and bringing it back to its former beauty. It is now in better condition that it was when delivered from the factory. But this was at a tremendous cost in terms of time, effort, and
money. For what I spent, I could have easily purchased a newer boat and saved myself the headache. However, this boat is a
classic; and my intent has been to restore a classic. Even restored and turn key, maintaining it is more costly than would be a newer vessel.
The bottom line is:
buying old and
cheap in the beginning will not save you money. It will cost you more than
buying something newer and paying more for it.
Unless you intend to own and baby a classic boat, my
advice to you is to buy something newer and less prone to
maintenance issues associated with older boats. I love my boat and would not consider owning a newer cruiser, but that's a personal choice. And if I was a first time boat owner, I wouldn't want to be owning and maintaining a "classic" as a first time experience.
Hope this helps...