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Like basically every discussion I've ever seen on e-readers on MR, this really depends on individual needs and tastes.
Wifi isn't a must-have for me, but it's certainly a nice-to-have. I don't particularly like having to fart around with a cable to download books to my Kindle, and I don't have to. I don't have a Web server set up like one of the previous posters, but I could see that as useful. You bookmark your Web server, you navigate to it, click the book you want, and it loads on your reader. You can have an expansive archive without having to use the cable all the time or download from some far-away website. But I can get why the one-time setup of the Web server might be more than some people want to do.
And while it's certainly possible to read library books on a Kindle, let's be honest: At best, it's a hassle. If library books are going to be a big part of your e-reader experience, there are much better choices out there for you.
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