I’ve run into this exact situation before, actually—thought my credit card’s coverage was bulletproof, but then the rental company hit me with a “loss...

Mileage-based stuff like Metromile does sound less stressful than the apps tracking every swerve and stop, but I get your concern about the dongle. I ...

I get the appeal of a laminated card, but honestly, I’ve had one get so worn the print started smudging after a year or two. I started keeping a photo...

Couldn’t agree more with this. I get the temptation to just hand over the keys and hope for the best, but insurance companies are quick to spot patter...

It really is a mixed bag, isn’t it? I’ve run into the same thing—one shop practically rolled out the red carpet, the next acted like I was trying to p...

I know exactly what you mean about the “deal roulette.” I’ve run into the same thing at different gas stations on road trips—one place lets you stack ...

Totally get that. Last summer, someone sideswiped my car while I was on a road trip—didn’t leave a note or anything. I snapped a bunch of photos, incl...

Totally agree about mentally planning ahead—it's a lifesaver, especially on longer road trips. One thing I'd add is practicing the habit of regularly ...

Haha, totally relate to the "cross your fingers" strategy... but honestly, insurance isn't something I'd gamble on. Learned the hard way after a minor...

Good call on the spare parts. Last summer, my mechanical pump gave out mid-trip. Luckily had a rebuild kit handy—got me rolling again in about an hour...