And everyone is entitled to their point of view
The way I look at it is this....I dont see Apple allowing Winterboard because of a few reasons.
1. Simply because it "masks" copyrighted images from Apple.
2. It is "technically" considered editing Apple's own apps. Even in a small way.
3. The way Winterboard runs in the background totally destroys all the "regulations" Apple has set in place with using the SDK and developing apps for the iphone. There would need to be a huge change in these "rules" to get it approved.
Im not saying its impossible, just unlikely.
Also, the creator (Saurik) has no interest in launching anything in the AppStore (At least not right now). So that'll kill it right there.
I also 100% agree about giving back to the creators/devs who develop these apps and themes....alot of them have ways of taking "donations" for their work. And I think they totally deserve it. As someone who also like to create themes and who is pretty versed in Photoshop, etc....I know how much time and effort this stuff takes.
I understand your POV with wanting to pursue this later and possibly make some $$.....But, look at it this way, since the iphone was released (basically)...people have been hacking it and creating themes for it.
It would take EVERYONE charging for that kind of work, before anybody would "pay" for that kind of work. Know what I mean? There will go were they can get it for free. Even if Winterboard was released to the Appstore...and themes were being brought to the Appstore....
You would still have a very large community of people doing for free....like they have been. Where there's a will, there's a way.