Most of the time it isnt gonna make a difference, I ride in any weather year round. 5 minutes of riding in the salt and slop and whatever chain maintenance is done goes bye bye. In rain you get a couple hours. Salt has an amazing ability to stick to chain lube Chain stretch still makes a bigger difference methinks.

Ever taken a chain apart after a few thousand miles? The rollers dont wear that much, but the side plates stretch a bunch. Ive broken a few, the rollers and pins were fine even with very little maintenance. As far as extra friction in the drive train, its negligible, you lose more just riding a geared bike with a derailler. So until the chain is dry and getting noticably either noisy or I can feel it when pedaling, I leave it alone. I can understand rec riders wanting to do it all the time though, for me, it just isnt worth it.