He's whingeing about GIMP. I agree both programs could be easier. Photoshop has been bloated up with stupid computer tricks to justify frequent version releases, but it's hardly improved since version 6. Of course the difficulty with designing software is anticipating exactly what all users want to do, so do you make a few features that are really polished, or many features that are pretty rough around the edges? It's probably the latter that is going to win you over new customers, since you can't return the product for a refund, when you find out it's not all it was cracked up to be.
Like Windows, Photoshop has a big installed base of people who have invested years in learning how to use it, so Adobe doesn't have to really try to improve it -- unless some competition comes along (which is why they bought Macromedia).
While I agree that using raster applications for vector drawing is intrinsically illogical, the developers have to an extent fed that illogic, by including tools (such as text and drawing) that possibly shouldn't be there. The fact that they can't do it usably is the sin, not the expectation of users that it should 'work' intuitively.
And drawing a vector in one application, exporting as an intermediate file, and importing into another application is a PITA. A workable/non-crashable version of 'live update' is more usable, but the most intuitive approach is to have it all there, in one application.