Why wouldn't you just charge the cases in a loading tray?
Definitely the easiest, but mainly because my reloading bench is in an outside garage, at the end of our street, among a row of garages.
Loading in a tray would limit the number of cases to 100 max, it would mean either loading them just prior to reloading because I don't want a bunch of unsealed cartridges lying around. If it is raining (or snowing these days), moisture could get into the cases.
Finally, and most importantly, my firearm hobby and my reloading practices are my business and no one else's.
Curtain-twitching is a national pastime for some around here and what I do is none of their bee's wax, so I don't want to walk around with .44mag cases!!