12,000km from a chain!!!!!
I usually change mine after 2-3000km. Maybe that's why the ring was looking "ugly"? You can't be too unhappy with that!
I have several set-ups having standardized all my bikes on Shimano 9-speed ranging from Tiagra to Ultegra (the previous version). All feel different and I'm particulary impressed by the Ultegra hub/freehub, although I prefer the 105 STIs.
However unless you are good enough that that 100g makes a difference then I wouldn't sweat it. I went for the stuff I did at each time because that's what I could afford. I still use the lower range stuff and don't partcularly view it as "inferior" or go "ugh" everytime I sit on my Trek 1200 with Tiagra. I certainly wouldn't stretch a budget or buy-up on tick.
It's probably better to say simply the more you pay, the smoother and more refined it feels, functionally no different, rather like fitting soundproofing to the same car. Realistically, it's often the kudos you get from other riders of having good kit, although there's something deeply satisfying about anihilating a serious looking rider on a Colnago with entry level kit, or better stil my hybrid with pannier stuffed with shopping!