I've had a pretty similar experience, actually. Military insurers can be great if your record stays squeaky clean, but the moment you have even minor ...

I've noticed the same thing. When I first started driving, military discounts were a lifesaver, but after a few years accident-free, civilian insurers...

True, but even with coverage, lending your car can still bite you financially. Personally, I'd rather pitch in for my friend's Uber fare than risk dea...

Went through something similar with my '72 Mustang. Regular insurance kept dinging me hard for minor stuff like windshield chips and small dings—got f...

I get the gambling analogy, but honestly, insurance feels less like dice-rolling and more like budgeting to me. I'd rather pay a predictable amount ea...

I went through something similar with my '72 Mustang. Thought I was being smart by sticking with the lower mileage policy and just paying the occasion...

True, luck plays a role, but you can still minimize surprises. When I switched insurers, I asked for a sample policy first—tedious, yeah, but it helpe...

Totally agree with the comfort-level point. Another thing I'd add is to actually sit down and crunch some numbers. Here's how I usually do it: first, ...

Had a similar experience a couple years back—lent my car to my brother, who's usually super careful. He scraped someone's bumper while parking, nothin...

Totally agree on the mid-range tires—I've been running those for years now, and they've never let me down. Honestly, I learned the hard way too. Had a...