I've also pulled many trailers off GL lots (Minot, Ripley, Sparta, Dodge, Letterkenney, Meade, Warner Robins, OKC, Rieley) never had a problem. That's not to say that problems can't come up. If you're prepared for them, the're usually not a big deal. Make sure the tires are aired up properly. If you can get one, have a spare tire with you (if the tires are good and the trip is short not so important) and check your hubs for heat regularly, just in case, and you should be ok.
That said, if you have a couple helpers (don't count on GL) with you, you can probably winch that 103 in the trailer. But if it has a pair of gennys on it your top clearance might be tight. And when it's inside the trailer you won't be able to watch it to see if it's shifted at all. Even when tied down well they can move or side shift on you. Could be a pain in the butt getting it backed out.
However you decide to do it, good luck.