I just went through this similar situation. I'm on AT&T now and got an HTC Vivid. Bigger than an iPhone, but smaller than all of these jumbo things that you are supposed to put in your pocket. Price was just lowered to $49.99. 4G LTE, latest Android ICS/4.0, really like the phone. I like the bigger screen, but hated all the phones that are even bigger - I don't want to shove something the size of a sheet of paper into my pocket.... This is a good compromise on size, with great specs and a great price.
If you are really tech impaired an Android phone may be a bit much for you to take. I think it's a great platform, scattered os but a great phone. Try the font change for a few days
I work for ATT currently and have customers everyday with the same problems your having. If you want a bigger screen with the easier to you software, then I recommend the new Nokia lumia 900 great device with awesome battery life and good sized screen. The best phone is the new HTC one x but the Android platform can cause headaches to people that aren't tech savy. Another option is the Samsung galaxy note. It's a full tablet and phone its massive but not to big IMO.
I think if you're going to just buy it and use it, get an iPhone. They're stable and they just work, like everything Apple. If you want to tinker, get a Droid, it doesn't really matter which if you're going to root it anyway. I HATED my HTC after 3 years of iPhone till i rooted it. Now its the greatest thing since sliced bread. I wouldn't go back to an un-rooted droid, or an iPhone, even if its been jailbroken.
With AT&T? HTC One X. Hands down one of the best Android phones out there, good size, 4G, great processor.
Good size? Where do you guys come up with this stuff?? Are you all carrying around man purses or something........?
There isn't much in the way of small Android phones anymore that would have a larger screen for him to read. Therein lies the problem. I carry an iPhone 4S because I don't like how big the Androids are going, but for his description, it would be his best bet.
Try to remember, it is just you Apple guys that wear the skinny jeans. Android phones fit in to normal size pockets.
Thanks for all the help guys. Dude at AT&T steered me ionto this one. Love it, easy to use and very easy to see numbers. http://www.greatcall.com/Jitterbug/Phones/JitterbugGraphite/