Haha I get where you're coming from... Uh kinda. But there's an issue with your logic. Once your natty system gets shutdown by the dbol/winny no amount of test boosting supplement is going to help. What's 0x100? That's right you can't boost what doesn't exist.
If you're just determined to do this, damned the consequence or advice anyone else is giving you, at least start from the beginning and read all the stickies on how to cycle properly. THEN we can circle back and talk about your plan.
Or do the dbol, for 4-6 weeks, bloat up with water weight, lose your dick for a while and when all is said and done, you will end up right where you are now plus maybe a few pounds. But my guess is since you haven't learned how to eat correctly to gain and maintain solid weight, you'll end up spinning your wheels for nothing.