[fjtorres]

I have both a PB360 and a Kindle2.
Both have their strengths and weaknesses and both are solid choices, especially the K3, which has addressed a lot of the issues I had with the K2.

Me, because the bulk of my reading is DRM-free, I tend to use the PB360 a lot more.
It is lighter, has better ergonomics (again, K3 is improved over K2), is more expandable and more customizable.

I would suggest that your first decision needs to be where you are going to get your books from. If you are going to get them from Amazon then Kindle has a leg up since you don't have to strip DRM or jump through hoops to get them onto your reader.
If you are going to rely on library ebooks, the ADE-based PB360 has a leg up for similar reasons.

Second, you need to decide how important form factor and portability is for you. The K3 is slightly smaller and lighter than the K2 and has the newer higher contrast screens while the PB360 is the size of a CD jewel case and is going to be a wee bit sharper because its 5" screen has slightly higher resolution (200dpi) than the 6" K3 (167 dpi).

Third, you need to decide how important customizability and hackability is to you. Both are comparable when it comes to DRM'ed content but the PB360 is quite a bit more customizable than Kindle, especially for DRM-free content. The PB360 has better onboard file management and allows you to use any TrueType font family to read with while Kindle offers up only three variants of the Caecillia family.

Finally, there is the issue of connectivity; the K3 has wifi (or even 3g wireless) for access to the Kindle storefront or your own PC and your personal library, while the PB360 relies on its microSDHC and USB to get content onboard.

You won't do badly with either; you just need to determine which features offer value to you and best meet your needs.