You imply that the applications are for Windows only and not cross-platform, in which case I think the answer to 3. - This is really not a good idea - trumps the rest.
The reason being you are going to have to extensively test the application under Windows anyway, either directly or in a virtual instance. That being so you're better to develop under the target OS because you're more likely to produce a better application - both from catching the bugs earlier and more thoroughly and ensuring your application 'works' for your users. I certainly wouldn't trust just Wine.
I'm not a big fan of cross-platform widgets. Like Java applications you generally end up with something that doesn't quite look right, and like the uncanny gap that can be enough to make your application smell bad to a large section of your users. Even at the slightly more abstract level, each OS's applications have a slightly different feel as to how they work and you'll most likely end up with a Windows application that feels like a, say, KDE one, which will again put your users off.
So yes, certainly possible to do this, but probably not the optimal approach from point of view of the quality of the end product. To do so will give yourself something of a handicap with what you produce and I'd say that's likely to offset the convenience to you of using a Linux platform. Actually I'd be surprised if you manage even that because I'd bet you'll spend more time messing around with the widgets trying to fine-tune them so they work right under real Windows than you'll gain from using an unfamiliar Windows toolset.