I only have one Alternator (Ricochet) and he is a royal pain to transform, so I can't imagine how a child would be able to convert him without cursing like a drunken bending unit. Sometimes I rationalize it by saying that smaller hands might be able to do the transformations a little easier, but then I look at those IKEA-esque instructions and wave off that rationale.
Brian, as someone who just recently fell back into the TFs with the Classics line, I can say that you need to set limits for yourself as to what you will and won't buy. I've only bought one TF since I returned to the line last fall that I regret buying (Titanium 6 inch Soundwave), and after that, I swore to myself that I wouldn't buy anything outside of Classics and/or the Movie line that I didn't really like. So far, though, outside of the mini-cons in the Classics line and the ancillaries, Scout class, and Real Gear stuff that isn't Laserbeak in disguise, I've stuck to that.
That being said, if I had to suggest any Classics stuff as a must-have, it would be:
-Voyager Optimus Prime
-Deluxe Bumblebee (based on what you've said)
-Voyager Jetfire (just beyond cool)
-Deluxe Starscream (because it's Starscream)
Or if you want to just act like a giddy kid again (which I can neither confirm nor deny I do when I got these), I'd suggest picking up the Robot Heroes line. Look at how little Shockwave is!

This may not be news to anyone, but I saw the first wave (Megatron, Bumblebee, Barricade) of the Robot Replicas series today at a local K-Mart. Sure, they don't transform, but they look pretty damn sweet.
I'm going to be all over these. Thank you for the heads-up, Neal. I'll wade through the debris at the local K-Mart and see if these are there yet.

Oh, and major spoiler for the TF video game which by all rights SHOULD translate to toys given how Hasbro is making so many characters from the game into toys....
Keep scrolling......Spoiler ahead.....
Shockwave. As a huge purple gun emplacement and very similar to a movie version of the G1 character in robot mode. Hasbro, make this ASAP.