Even if you gain weight, that cutting process will be even harder. And you'll most likely stall at that 220lbs mark as before. I can relate, as to this point I've stalled at 170lbs for several months. But through an increased caloric deficit I pushed through it and I have been losing weight again.
Yes your stomach will still be a little flabby if you cut calories dramatically. That's why you do it gradually and make this a process that happens over time. Personally I think you should not bulk, and just stay at your existing weight, and keep weight training. Build more muscle in order to increase your metabolism. That, and you might make wiser food choices (if that is an issue) and eat low-cal foods and no/low-cal drinks. With a concerted effort and some consistency you can break through that 220lbs barrier.