I love the 551 D2 vs. Ritter Grip reference. I went through literally the exact same conundrum a few months back. I have a well-used 551 in D2 I got at Cabelas - it's been everywhere with me since college and was my first "nice" knife. I got a Ritter Grip in M390 thinking it had to be better than my old trusty 551. Well, I found out rather quickly that the M390 would do nothing to replace the memories of hiking, camping, sailing and traveling with the 551 D2. So the Ritter went on to a new owner and I'm perfectly happy knowing I kept the knife with the memories instead of the knife with the super steel.
Great suggestions here and I'm in the same boat as you - looking for ways to "enjoy" knives while not buying superfluous items. I've found that the stories from others, reviews, and getting into sharpening are helping (at least for now).