Okay, I'm back from the Costa Rica project and I'm ready to buy those accessories I was holding off on. So I read up on them a bit more, and the official Apple accessories are quite a mismatched lot, aren't they? So much for all their design and "it just works".
As I said elsewhere, my iPad was a gift, and the gift came with Apple's case. Although I would agree the case is a little flimsy when used as a stand, I actually like the case when it is used as a case. A nice book cover - even the air steward on the plane last week was asking where I got the case from! (he'd only bought an iPad on its own). I intend to try some screen protectors and have some on order. Finger prints are the big problem in that department, although protection from sand/etc scratches would be good.
So do I need a dock and/or a keyboard? I was thinking of the combined keyboard/dock but it only works in portrait mode and I mainly use my iPad in landscape (the Kindle app being the big exception). Also it doesn't work with the case(!), and it doesn't look the most practical design.
However the "dilemma" in the title is more of a philosophy dilemma. Why have a keyboard on an iPad? What is the iPad good for? It is great for consuming content and a handy very portable form factor (more practical than an iPhone but much smaller and with much better battery life than a laptop/netbook). Web and email stuff requires key entry. The popup touch keyboard was better than I expected but it is limited for lots of text entry (eg. all but the smallest emails). So a keyboard could be used for this kind of text entry, but this rather reduces the iPad's portability. If I am at home and need to write a long email, then I will use my laptop or my main dev PC (which I'm typing this on now). If I am travelling, then taking a keyboard with me could be very impractical - I might as well get myself a Netbook or take my laptop.
In other words the keyboard attempts to turn the iPad into something else (poorly) and at the same time loses many (most?) of its advantages in the process.
(as for keyboards, it would appear an Apple Bluetooth might be the better option but Apple never thought to list the physical sizes of their keyboards on their website - just things like "20% smaller than average"!)