Bear in mind that recumbents are not great on off-road situations; whereas on an upright bike you can always lift your weight off the saddle when you see a bump coming, you can't do that on a 'bent.

Also, bear in mind the common lore that recumbents are bad on hills. There is some truth to that, but not so much if you spin a high cadence. Basically if you get up hills by putting your weight on the pedals, you won't like a recumbent because you can't put your weight on the pedals.

I'm not an expert on recumbents. I have one, an old Counterpoint Presto, but it's the only 'bent I've ever ridden. My advice would be to try to ride some different 'bents, both long and short wheel base, as many as possible, and for a minimum of 10 - 20 miles on each (preferably a lot more).

It takes a while to get used to riding a recumbent; the hard part is that you really have to relax your whole upper body, and "just relax" is easier said than done. When I got mine, last summer, I did a few short rides around the neighborhood to get the feel of it, but I really couldn't tell what it was good for until I took it for a long ride. After about 70 miles my arms were so tired I had no alternative but to relax them and then, finally, I started to get comfortable. When I got home my odometer read 100, and my legs were painfully tired, but I was comfortable.

The novice will almost certainly be unstable at low speeds (I sure am), so it is hard to make tight turns; I haven't tried it with a trailer, but obviously that would be even harder. It shouldn't be impossible, but I'd suggest you don't try it until you're comfortable on the bike in all other respects.