Anyone else really hate Winchester's game? I mean, I can typically get two or three of them, but something always prevents me from getting the fourth one. However, there are tricks/secrets to get past his annoying game.
After playing too many cycles I've come to the conclusion that a lot of the most useful items for Winchester are in green chests. These include the Ring of Ethereal Form, Wax Wings, Hip Holster (what I use in this video), along with a number of really awesome guns/items. The last bit of advice is to always do Winchester last, unless you don't think you'll live long enough to beat the boss. I say this because, I actually got a Jetpack on a floor with Winchester from the boss, so sometimes you can/will luck out.
As for doing Winchester's game, the best items are the ones that make you fly (Jetpack/Wax Wings/Ring of Ethereal Form), since you can fly next to the items and shoot them. The next best item is the Hip Holster, as it basically doubles your shots. I'm not sure if there are other ways to cheat, like shooting shells/Meat Boy blades into the game area, but I can confirm these four items work.
Anyway, good luck and eventually you'll find floors with him or the secret store. I've also never seen him on the fifth floor, so he either doesn't spawn there or its rare. In either case, I strongly suggest just not going there in general.
