Thanks for the responses everyone. This forum is a wonderful resource.
Your reply was very helpful. Concerning annotations, will the eBookwise at least list where in the ebook you've made annotations? In other words, is there a function to jump straight to pages with annotations, or do you just have to "flip through" the book to find them (like a regular paperback)? You can tell I'm a complete noobie here.
Whatever the case, I think you may be right about just trying it. $2/week for a year is a good way to contextualize the purchase. EBookwise also has this sort of cult following which makes me think it's pretty solid, so long as you can endure the LCD display. The 64 mb factor still worries me a bit, but one can only read so much about ebook readers before actually trying one out. Knowing my luck, 1 month after I buy the thing, the dream ebook device will come out for $120, but as you say, $100 shipped is not a real big risk in the long run. I kind of feel that ebook readers are in the same place netbooks were about 18 months ago--just about ready to get refined features and a 1/3 price drop. But then I sense that all the neat stuff is still going to cost >$200, and one could wait around forever for the next big technological advancement.
Does the little keyboard for the Kindle really work pretty well? And do the annotations sync back seamlessly with the Amazon servers? It really is a tempting device insofar as everything just seems to work well for people without a lot of rigmarole, but being the cheapskate I am, I cannot bring myself to shell out $260 at this point. Probably not a real great chance for a 30% price cut in Q1 2010, either.