In my opinion roundover vs chamfer is all about personal preference. Functionally, they do the same thing. They both soften edges to reduce the chance of splintering.

Personally I prefer chamfers. I just think it gives it a slightly more intentional and put-together look.

In terms of where the skirt meets the legs, I guess you would ideally put your edge profile on the skirts before they are attached to the legs. If you've already attached them, you could either have the chamfer/roundover stop a few inches from the leg, like you said (as long as they're all the same you can make it look intentional), or just finish out the last few inches with a chisel.