So, back on the wagon.
Got a new diabetes educator who suggested some changes to my medicine regimen. Logging everything I eat -- which by itself forces me to be more careful about what I'm eating, even if I'm not actively picking the best foods.
Walking a few days a week. Waiting on the gym until school is out so I can more easily work it into my schedule (also helps me ramp up with the walking instead of jumping in full steam)
Doing 100pushups.com's regimen for pushups again. Finally made it back up past week one day one.
Back down to 265 as of today - had this goal for about 9 months, but was pretty much steady at 275 since August; dropped the 10 pounds since the doc visit a month ago. Next goal: 255, as I crawl back down 10 pounds at a time at least to the 225 low I hit with medifast.