I believe obsession with upgradeitis depends on the person. I have been obsessed with modifying everything I have owned from the cradle and it became my livelihood...product development. I have another friend that simply buys a road bike and rides it. He is a good rider as well. He also performs 1/10th the maintenance on it I do...never takes the cranks off, re-cables the bike, rarely changes a chain etc.
So there are clearly many walks...as expected...the way society rolls.
Me? This winter I am obsessing about stripping the Campy 10s off my new bike and installing Ultegra Di2. This is part is to change my cassette to a 28t in back...Shimano has more cassette options...but that really is just an excuse...lol. I am also perpetually fiddling with my fit on the bike...a mm here and a mm there...always searching for the holy grail of best position 'for me' on the bike. There isn't any of course.