If you have a Barnes and Nobles near you, go check out a nook.
I really like my Kindle. It's great for the technically disadvantaged in that's very simple to use.
Turn it on and it opens to where you were reading when you left off.
Reading is a simple as pressing the Next and Previous buttons when you want to turn the page.
I buy my books online rather than directly from the Kindle. Take a look at Amazon's Kindle section. If you are setup up on amazon, you can buy any book with a single click and it will be delivered to your Kindle in about a minute.
Read this page and watch the videos:
http://www.amazon.com/Kindle-Wireless-Reading-Display-Generation/dp/B0015T963C
It tells you all about the Kindle. I have the smaller version which is $189. I like the size because it is about the size of a paperback book.
I leave the wireless turned off unless I am buying a book. With the wireless turned off, I only need to recharge it every couple of weeks or so. Turning the wireless on/off is simple.
It's easy to learn even for the technically disadvantaged. Forget about all the tech stuff. In it's simplest form it's just a book reader.
It's not perfect and there are advanced things I would like to see it do (better bookmarking for one).
I normally read several books a month. I haven't purchased a real book since I got the Kindle at Christmas.