I've now been running Ubuntu for over a year for my own side business, for my consulting gig and as a student and I haven't had any issue I couldn't solve and one of the main solutions is to bow to the majority in some cases and use emulated XP or WINE.
The new ubuntu has better font smoothing by default however I don't think that transfers into wine sadly but at least you found a setup that works.
It looks like Photoshop isn't quite there yet though: http://www.codeweavers.com/compatibility/browse/cat/?cat_id=...
It is one of the top applications that they are working on: http://www.codeweavers.com/compatibility/toplists/
If I remember the Wine Weekly News report correctly, I think Disney wanted it working on their Linux machines they used for rendering, and committed back all their fixes to Wine. So whatever that version was is probably pretty usable.
The main obstacle for migrating completely is a handful of the usual software titles, and tablet support. For tablet computers, like it or not, Vista is still the best, hands down.
But my jaw just dropped with the out-of-the-box support in Jaunty. It is marvellous. If multi monitor works just as smoothly, today might just be the day.
How well does VMWare work for you? My guest OSes are always as lean as possible with all graphics stripped out, and they are still laggy.