I upgraded between five and one year ago. I bought one piece for my son five years ago who was going to a camp, certain size needed that we didn't have and loved the four wheels that move any direction, just found that so much easier to manage. We do about four trips a year, maybe six for DS. Anyway, before a long trip to Kauai, I replaced our two large black bags with the two wheels (I really didn't like the bags either) with the four for the same style and model that I had gotten in the smaller case for DS (just loved that bag) (about thee years ago). I just really found these easier to mange than what we had had before. Since then too, just before DS did a summer abroad trip studying photography where we would be carrying and expensive camera and lenses, I bought one of those small hard sided bags, with the four 350 wheels, so I have four bags altogether that are five years old or younger. Traveling can be a big hassle and if updates in technology make it easier with easier to maneuver luggage and you can justify the expense in the ole vacation budget, I say go for it. // And I'm very sorry to admit (sounds vain) that I do take pleasure in looking at our luggage on the carousel (on every trip since we've gotten it I have said to myself) -- oh that luggage looks so nice, I love those bags, they have really made traveling easier too.
I think the better deal in luggage too, are some pretty good brands on sale vs. more discount pieces full price (price difference isn't that much). I'm not talking anything that extravagant either. I bought our luggage at Macy's -- just found that one piece that I was gaga about and within two years replaced two old big bags I really didn't like with stuff that matched that. And as stated I also got something else too I wanted specifically for Italy travel for DS we didn't have. Oh and I almost forgot too, last January before going to a wedding in Idaho -- family -- I was a reader, etc. we got a wheeled suit bag that also stands up on it's own -- really cool and kept the clothes so nice and not wrinkled -- had way more nice clothes to bring on that trip with the special dinner and wedding. Found that bag great for going on a cruise the next year too. // They have made enough significant improvements in the past decade that I'm really happy about having upgraded. If you like what you have, though, and it's practical go for it. // So far cross my fingers, the new stuff has held up very well. -- but we are just talking like four to six trips per year.