Maybe try something like P90X or the Navy Seal Workout. You would probably lose some strength when performing a one repetition bench press but you would likely be more fit. Personally, I would rather be able to do a boatload of push-ups rather than benchpress a large amount of weight. It just seems more useful and functional to me.
I think it is smart to get trimmer. If you carry that much weight for years and years, you are probably going to develop osteoarthritis of your knees and hips when you are older. In addition, if you get injured or when you get older and have a slower metabolism or when you have less free time to work out (career, wife, children) you will probably put on quite a bit of weight because I would bet you are consuming quite a few calories to weigh 250 lbs. while working out.
Try to pick something easy and quick (30-60 minutes). A military workout with a lot of sprints, pull-ups, squats, push-ups can be performed quickly and with little equipment. When you are done with school and have a demanding job and have a wife and children with family responsibilities, time will be a factor. You need something quick and dirty. Just my 2 cents.
"Be of good comfort, Master Ridley, and play the man! We shall this day light such a candle, by God's grace, in England, as I trust shall never be put out."
--Hugh Latimer, October 16, 1555