Does the 20 fit in your car? If so, save yourself some dough and stick with the 20, especially since you already know how to play it well.
Think of all the 20 players in the Jazz idiom, many of whom used 22 or 24 if there was room for it, they could fit it in the transport and the band was full-size. I personally prefer 20,12,14 because it is considerably lighter to carry, but in a larger room, I used to move up to 22,13,16 in a heartbeat. 20 works for almost anything though, if you want to have a versatile drum.
As kookadams said, the jack-up thing can be a pain, though most guys didn't use jacks when 18's became popular (and you could have used a swivomatic pedal that can adjust to any size bass drum - little swivo plug in here).
Then if you get the 18 and need a bit more umph, you could be out of luck. I had a set of Rogers with an 18 and I let it go because the 20 was so much more practical for all-around play. Of course, where I am living (KSA), I can't play anyway, so doesn't make too much difference right now.