I keep mine mounted year round for 1.5yr now. I ride both in the day and night, so I am too lazy to take it off. It seems to hang on tight even on car trips. But I did notice the o-ring that mounts the light has lost some strength and elasticity. Most likely due to heat and UV. I would probably replace it soon...not because it might break and fall on the freeway, but its not keeping the light pointed in the right direction after a big bump.
I think with clamp type mounts like the gloworm, you probably wont have that problem.
Depends on the bike. I bikommute, so my road bike and my multipurpose commuter bike (rigid Cannondale MTB) always have lights on them. My third light set switches back and forth between hardtail (longer rides) and FS (bumpier rides, some long rides). I usually carry a couple blinkies or other taillight in my pack instead of leaving them on the bike when I hit the dirt because I'm afraid I'll lose them on a bump and not notice until I get back to the pavement - and by then it's 90 minutes too late. My spare headlight always lives in my pack if it's not being used.
It stays on most of the time as I need it for weekly commuting. If I'm going to hit the trail during the day on a weekend I'll pull it off. Takes less than 5 seconds to remove a gloworm light and battery if you've got the quick release mount.
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