I was pretty nervous aboout a paddock stand too when I first got my bike. That and a flip-up stand too...
Especially as I'm just a slip of a lad, not like some of the pie-eaters around here...
But I'm OK with it now (although, funnily enough, I nearly had a "moment" a few weeks back when using someone else's stand, obviously with a slightly different movement).
But shurely with a trailer you "can" ride the bike straight on (I'm sure you could on the ones I've seen)?