I've always carried insurance on everything. 7 years ago my Shop burned completely. Inside were my 3 yr old Dodge Cummins truck, 2 Jeeps, 2 tractors, 2 ATVs and all my tools/shop equipment. It turned out to be a $193,000 claim. I was 57 years old at the time. Without insurance I would have never financially recovered. With proper coverage it was only a slight setback and within a year I had fully recovered with a new shop, newer truck, Jeeps, Tractors, ATVs and a full line of tools/equipment.
I'll always have proper insurance coverage. And, if I never have another claim in my life the premiums I'll pay will be a very small percentage of my $193K claim. No brainer to me. I think anyone who has had a large claim would say the same thing.
Gamble all you want. Just don't whine when it goes bad.