I think it can work well to bulk and cut in the same cycle. Just do all your bulking first, then think about cutting. Get your both done before you come off (i.e. give it enough time to do both without rushing). In some ways I see it as much safer to cut while on. Too many people get anxious and cut too soon after pct and do it wrong = muscle loss.
You could do something like
Weeks 1-4: SD 20mg ED
Weeks 1-12: Test E 500mg EW
Weeks: 6-12: Winny at an appropriate dose
Follow with pct.
Bulk for the first half, cut for the second half, the salient point being that most people seem to throw winny in at the end of the cycle for maybe 6 weeks to cut with. Keep in mind though if you have a 12 week cycle and only bulk for 6 weeks of it, you limit what muscle you can build.
If you use SD and winny together in the same cycle make sure your winny is not methylated, get injectible winny.
Alternatively, I don't see a problem with following 3-4 weeks of superdrol with a 6-8 week prop/winny cutter. That wouldn't leave you as much time bulking though and you wouldn't have a base of testosterone the whole time (unless you started the prop at week 1).