I have both, but I don't use the trailer unless I'm hauling more than two boats. For me, throwing a couple of racks on the car, followed with a couple of boats is easier than getting out the trailer and having the manuvering and parking issues. It's not inexperience, I've had many trailers over the years, from utility trailers to a 28' camper.
But my boats are light, my health is mostly still good,and I'm tall enough where the reach isn't too bad even if we take the truck.
My trailer for the yaks is an old (1965) 18' galvanized boat trailer modified for kayaks and/or canoes, so it's not the lightest thing in the world. But it was free, so there it is.
Your equipment will be different, so you assesment will be based on what you have available, I'm sure.
Pull-Up Strap Handle Kit
Canoe / Kayak Anchors
Touring Kayak Paddles
Sport Cases (Electronics)
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