Upgrading our technology - What's a frugal late adopter/laggard to choose?

Despite my best efforts to ignore the advances in technology, it is time to consider make some updates to computer, phone and perhaps to add an E-reader or tablet. As usual I am relying on my technically adept son to help with advice but I am really starting at a low point of knowledge. For example, I had to ask him how you access wireless service if you get an E-reader. He says he has an extra wireless router he can ship me. Still not sure how that works with our internet service.

Anyway, here's what I am thinking.

Easy - Computer could use a new keyboard although the current one works fine. I've asked said technically savvy son to give me one for Christmas. At least all the keys would have readable letters on them then.

Middling Difficulty - I use TracFone for mobile service as I only use a cell phone when I am out of the house. My old cell is a very basic phone - no internet access or other smart phone services. I have lots of prepaid minutes I'd like to transfer to any new phone. I haven't sat through the interminable wait to talk to customer service yet to see if that is possible but I have asked same son to tell me if any of the phones they currently offer might be good for me. Step one at least.

Most Difficult - I like to read and listen to music when I travel. I hate spending money on books as I am an avid library fan. I do think that I would like to have some sort of device though that brings me reading material on the go. I've asked my book club for advice in choosing between a Kindle Fire and a Nook HD and so far don't have any clarity. My son threw in the Google Nexus 7 as another option. Oh my aching head (from pounding against the technological horn of plenty). UPDATE: My hubby found this great LINK to help think through this question.

Advice? Experience? Suggestions? Any and all help is appreciated!