Leave strap on or attach each time

I used to keep them on all the time and had similar experiences as Larry. Ditto with any metal fittings, rivets or grommets. I do have straps with plastic parts.

If you practice putting a strap on and taking it off a few times by approaching the pin by pushing one side of the hole/slot under the pin edge, then sliding the other side over the top, it's not very stressful to the pin or the strap. If you really struggle gettin it on, you may have to enlarge the slit by an 1/8" with an X-acto or scalpel. The hole will wear and enlarge over time. I use silicone "washer" type strap locks to prevent the strap ends from coming off the pins while I'm playing. The metal pins without a mushroom head are particularly worrisome.

The outgassing and chemicals in tanned leather can react with the finish. Especially if the tanning process is badly (cheaply) done. I also had some man-made vinyl type ends with glossy materials squeak and stick to a high gloss finish. A fine grit abrasive will rough up the surface of the strap ends and stop the squeak.

I leave the strap on if my uke is in a wall hanger or floor stand for a day or two.
 
While I don't play ukulele with a strap, I do leave the strap attached to both of my guitars (electric and acoustic) all the time. It's been perfectly fine. However, it may not fit into some cases with the strap attached.
 
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