Yuo can gain and cut regardless of whether you take winny (or any steroid)... yes it will help... but you will find most people will advise against it as oral only courses are limited and put alot of stress on the body...
If you do a lot of endurance work and have a tough body DON"T do Winstrol. It is terrible for your joints. It will make your ligaqments a lot thicker but they also become very brittle as Winny prevents the proteins cross-linking. A good drug (which I really like) is Anavar. It won't make you put on lots of mass but it will increase your strenght a lot and you won't put on water bulk. Plus, Var has a minimal effect on your natural test production and is easy on the liver (by oral steroid standards) so you could happily run for 12 weeks without any problems..
In general it is a bad idea to run more than one oral at once as they tend to be 17 Alkylated which makes them liver toxic. Some are worse than others; Anavar is easy, whereas Anadrol is brutal on your liver. However, Primobolan Acetate is an oral which is not 17 alkylated and is not toxic as a result. However, because it is not 17 alkylated the liver destroys a lot of it so you need to take quite a bit. Its also pricey..
You can get sublingual (don't swallow or your liver will destroy the steroid)testosterone tabs that aren't toxic that should work as well (I've never tried them though)..
If you want to run Anavr then I'd suggest 40mg/day split through the day. By the way Anavar and Primobolan are very good for bone and ligament strength as well as muscles. They both very low in side effects (although anavar my my farts smell disgusting for some reason but maybe thats just me )..