OOh, fancy! I think "breaking in" is basically enduring a bit of agony while they stretch enough to accommodate your feet. I'd do what I used to do with my old leather skate boots: wear them around the house every day in small periods of time, as they might totally destroy you if you bring them to a full-on 2 hour session for the first time. It may be boring, but probably worth it?
Another thing you could do is fixing the outdoor wheels and going for short skates, as the irregular terrain might encourage the softening of the skin (hopefully in the shoe, not your feet). Gel pads are definitely worth considering, yes.