Rode to the dojo, gi (aikido uniform) bag and bag to carry bike stuff (locks, ID, etc). Cargo weight was 25-30 pounds (plus trailer & bike). The ride it self was uneventful. On climbs I am geared almost to the bottom but this cargo weight seemed to be a bit more cooperative all the way around (unlike the 45 pound grocery run a couple of nights ago). Can almost get out of the saddle with this weight. I still have to be very attentive to the bikes need's and bike to that.
Locking up is something that requires extra advance planning. I am currently using two locks and a six foot looped cable from Kryptonite. The U-lock locks the bike up (frame and both wheels). The second lock and the cable lock the trailer up (frame and wheel). I am try to find two (secure) poles that are 4-6 feet apart so I can lock up with the trailer still mounted. Then I can lean the whole thing against the two poles and they don't go anywhere as I lock the beast up.
Maintenance issues on the trailer itself: In the course of the last couple of days the trailer has successfully thrown both rear reflectors that it came with. the mounting piece is there, the reflector has slipped from the mounting piece. I have subsequently used Red and Yellow reflective tape on the trailer to make it more visible (most easily found at Wal-Mart. Other choices are Ebay and some Reflective Tape retailers online). The rear fender got a big piece of it.
I lost one of the machine screws that hold the fender in place. I have the the one cranked down. I'll have to go to the hardware store and find a couple more (and some lock nuts to got with it).