Here is a thought- pickup a cheap Lee Loader. In the comfort of your warm house you can charge your sized/primed cases one at a time and use the Lee Loader to seat the bullet. I would leave the OAL very long, just seat the bullet enough to secure it in the case neck for transport to your press where you can seat it to the final OAL and crimp as needed.
I would prefer this to batch loading a tray of cases and then trying to get the tray 150yds down the way without spillage. Plus, I always prefer single piece loading to batch loading. I like the freedom to stop whenever I want and know that only one case is in process. If the phone rings or someone knocks at the door or the wife needs something I simply dump the charge I am working on and step away. From a process standpoint, I have a serious aversion to rows of charged cases sitting on my work bench, but then again I was a process engineer in my former life.