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If you get an eReader, of whatever design, there are some sites about which you really must know. Collectively, they will greatly enhance the quality of your life as an eReader user.

I previously mentioned Calibre and Sigil. If you get a Sony Reader, you must, lest you imperil both your sanity and your sanctification, download Calibre. Calibre works with all manner of eReader devices, so I highly recommend it whatever device you get. 

I never got around to testing out Calibre with Dad's Nook, because the drag-and-drop method of loading material from the PC to the Nook worked just fine. But Nook users should still get Calibre, because (trust me on this) you'll really want your documents to have accurate metadata, given that Nook has no mechanism for organizing said files. A lot of files that you self-generate and/or get for free online will have incorrect metadata, so you'll need to use Calibre to fix them.  (Metadata = the tags within a file that tell you the title, author, etc.   It's what displays in the eReader's menu. If it's wrong, you're not going to be able to find anything.)

You can take this to the bank: when (not if) you have problems with your device, your fellow users will always, ALWAYS be more helpful than the help desk staff of whatever corporation sold you your device. The fine people at the MobileRead Forums provided me with elegant and effective solutions to sticky problems with both my Sony Reader and Dad's Nook. Hooray for teh interwebs!

MobileRead Forums are also a good place to start if you want to do some hardcore comparison shopping to find the device with the array of features that best matches your needs.

The store associated with your device is not necessarily always going to provide the best deal on the particular book you want to read. If you've got a Kindle, you're stuck buying from Amazon (which, as the 500-pound Gorilla of the publishing industry, pretty much always has the lowest price anyway); if you've got anything else, an easy way to comparison shop is to go to Inkmesh. It's like the Bookfinder of the eBook world. Their search is not comprehensive (at this writing, it does not yet include the Google eBookstore), but it's pretty thorough -- sure beats having to separately click around to a dozen different independent eBook seller sites. It's also a good source for links to FREE eBooks.

Google Books is of course primary (although now that they've integrated their eBookstore into the feature, I'm having trouble figuring out how/if you can limit your search to free eBooks only), followed closely by Project Gutenberg. ManyBooks has a very nicely curated collection. University of Chicago Press puts out a different free eBook at the beginning of each month -- if you sign up for their mailing list, they'll send you an email telling you what it is. (N.B. a lot of free eBooks have formatting problems; a lot of formatting problems can be cleaned up a fair bit using Calibre and/or Sigil. But you have to decide whether it's worth your time.)