A minute or two each time. Hardly a factor in the decision.
If I trailered 50K miles per year, then I'd need to grease them more often. Still not much effort, time, or cost involved. It's all DIY if you have the Bearing Buddies or similar system.
If you need a folding trailer, that's a different factor entirely that has nothing to do with the couple minutes of maintenance time difference.
1 Canoe/Kayak Trailer
Gedi Convertible Helmet
URCHIN Portable Anchor
Electric Kayak Motor
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