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Fuse - actually, Photoshop CS5 (the most recent version) does have a 3-d painting option. It chugs with anything too complex since photoshop isn't designed for that or especially efficient, but you can import 3d objects, spin them around and rotate them, paint them, etc.
I don't think that would be useful with the free version of Sketchup, as it cannot import obj. Actually, I'm not sure that Sketchup Pro can do it, either, come to think of it.
The major problem with texturing in Sketchup is that it doesn't have any UV tools. Without the ability to unwrap the model, you have to texture each surface individually, and it's difficult to get your seams to look natural. I'm afraid I can't really offer any advice on SU texturing—I've really only used it to pull geometry out of the 3d Warehouse for use in Maya (easier said than done, by the way).
What can Sketchup import and export? There's a tool I've used a lot for UV mapping (link) - I think it's pretty excellent. If you could create your model in Sketchup and then export to a format it can read you can set up your UVs and then go from there. Of course, it depends on what your eventual use will be. If Sketchup can't edit UVs maybe it can't handle them at all? From Ultimate Unwrap 3D you can certainly export to something useable by *most* renderers, however.
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Blender has an unwrap UV mode too - you then export the bitmap, paint it up and then apply it back on and hope like hell it lines up. Which it should do of course.
I'm going to give ultimate unwrap 3d a try first and then if that doesn't work well I'll give blender a go.
I'm kind of new to the 3d scene, so I'm not familiar with all this jargon. Thanks for all the great suggestions guys. If I get any decent results I will post.
Basic Sketchup only uses Collada, wrapped in Google's kmz format (if you change the .kmz to .zip and open the resulting archive, you'll find a Collada .dae inside). Sketchup Pro can export to several formats, but I'm not sure how it is with importing.
If you go the Blender route, I suggest you download version 2.4x not the new beta. I haven't been able to import a Sketchup model into version 2.5 yet, but it's relatively easy to get it into 2.4.
To clarify the jargon, UV are the coordinates in a model's texture space, which are separate from its coordinates in 3d space. Imagine a simply poly plane: it can be oriented however you like in 3d, but a texture applied to it remains in place. This is because the plane has its own set of coordinates, designated U and V (rather than X and Y). When you have a more complex model, it still has UV coordinates, but they're folded up within the 3d space. When you unwrap the UVs, you're essentially taking the model and unfolding it so that it will lay flat. Like a box made out of paper; when you unfold it, you'll have six sides all facing up, and you could paint that that and fold it back up.
Slightly bevel all of your edges and the corner's will catch the light better :)