My take? I like sweet rides. But the relationship between money spent and that ride is pretty loose. The five best rides I have owned are: my racing bike, a Fuji Pro that cost me $450 as a bike shop employee in 1977, my '79 Peter Mooney, the Reynolds 501 Peugeot sport frame I picked up for $20 badly damaged and set up as a fix gear for almost nothing, the ti custom road bike I paid over 2k for the frame and put on mostly used parts and the ti fix gear for roughly the same price (to replace the Peugeot fix gear with a bike I trust in the hills).
Somewhere close to these bikes are my winter fix gear, a '83 Trek 420 that represents about $700 invested and far more in routine wear and replacement and my (new to me) Raleigh Carlton Competition ($80 for the frame, and another say $400 on this and that.
Prior to the ti customs I had never spent $1000 to put a bike together, though quite a few have passed that mark in maintenance and replacements. And the ti bikes aren't about having xxx$$s of bike, they are about having a custom frame that fits and disappears under me and has the wonderful ride of titanium which I experienced 20 years before my first ti bike. Employment and money have been a challenge for me. (Some poor choices and a very serious head injury.) I learned to manage my money and trim down my life to simple, almost everything paid up front (I did take out a small mortgage for my house and bought the new car, a Prius, that should last the rest of my driving years with a loan for less than half the cost at zero interest.) While I was working a good job, I bought my two ti customs, bikes I have wanted forever.
Planned future expenses on bikes? I would like to repaint a couple, maybe have the Raleigh replaced with a new custom if it does not pass inspection. (It is being stripped for repaint. My framebuilder will inspect it before and after stripping, do a couple of minor repairs/mods if the frame is a keeper and build a new one if it isn't. It's a gravel bike and we have descents with serious washboard at the bottom here. I want a frame I can trust. I've lost too much of my life to frame failure. My fork failure 35 years ago cost me FAR MORE than a custom steel frame! In fact, an ambulance ride and three days in the hospital would cost me more even after insurance.
Yea, I have spent some real money on bikes. But those bikes have also been tools for me. Tools that have been a link to sanity, that have taken me places both physically and spiritually I would not have seen otherwise and tools that have gotten me to work, to friends, to stores, etc. (And my bikes only get flipped with me aboard; I try my best to NOT do that! They get ridden into the ground and retired.)
Oh - and that sweet ride and wheels? Man, you can make a sweet ride from quality aluminum rims, hubs that haven't changed much in concept over the past century and some formed and threaded wire. Using techniques more than twice as old as I am. And yeah, a set of wheels, new, will cost me roughly $300. But those rims will go ~5-15,000 miles, the spokes 15,000 miles and the hubs 'til I can no longer get bearing replacements. (I am happily riding a front Campy Tipo from the early '80s and I have a Sanshin hub from my Fuji that is still rolling.)
Ben