I've got friends who seem to buy bikes more often than I buy running shoes (and I buy a decent amount of running shoes). I get the whole N+1 theory, and there are certainly bikes I'd like to buy, but instead of purchasing a whole new package, I decided I'd upgrade my current frame a little at a time.
Twelve years ago, I purchased my first decent road bike: a Fuji Roubaix 1.1. I studied up, talked to local shops, and then was fitted for it at a locally-owned store that I trust. Then...I moved to NYC. After less than a month in Brooklyn, my bike was stolen. When I went to the police, they essentially laughed and told me that professional thieves can pop a U-lock in between 2 and 8 seconds (they showed me how). Professional thieves? I was heart-broken: my first NYC scar. I bought an all-black $500 Fuji Feather single-speed with zero bells and whistles to commute on, and a $90 Kryptonite lock. I used my bike for transportation only.
After a few more years in the city, I decided to look into road bikes again. I tested several out, but really just wanted my Roubaix. I found a Fuji dealer in Manhattan and they got me my bike. I vowed never to let it out of my sight: never to lock it at all. If I had to go indoors anywhere, I carried it on my shoulder. I started doing some bigger rides up 9W and with the local Rapha club.
When I moved to Colorado, though, that's when I really started biking. That's when I fell in love with big, long climbs. I live between Fort Collins and Boulder, which means access to some of the best roads/hills in the Front Range. I met some great people via Strava, and got some advice on parts. Over the past several months I've added the following: SRAM Force Outer Ring, SRAM Powerglide Inner Ring (34Tx110mm), Shimano Ultegra RD-R8000 Rear Derailleur, Shimano Ultegra CS-8000 11 speed cassette, Fulcrum Racing Quattro Carbon wheels, Specialized Power Expert saddle. This setup is like a new bike, but with the frame I've come to, and continue to love. I can't recommend the Fulcrum Racing Quattro Carbon wheels enough. Fully carbon wheels are insane. Basically, no matter what bike you buy, unless you're spending more than I did on my last car, you're probably going to get crappy wheels: it's how bike manufacturers save/make money. Straight up: the wheel upgrade is the best thing you can do for any bike.