I only have the regular Love size. It depends how much you carry, the regular Love fits quite a bit, I even have a large Hobo wallet and the regular size still works for me.
The regular Love is a good size to wear as a long strap shoulder bag (it's too short for me to crossbody at 5'7" but you probably could if you are shorter), I'd say it's roughly equivalent to the regular MAC or Affair, other styles I have, and fits a similar amount of things, maybe Love just a little less due to being more structured.
The Jumbo size is a little big for me personally to like wearing as a long strap bag, it is similar to the Large Affairs which I always wear with doubled strap, this style I like doubled strap though. The shape of the Love IMO doesn't look as good when you have to shorten the strap and wear under your arm, it's definitely much boxier than the Affair style is, so that's probably another reason I think it works better in the smaller size.