Chose the mid 2012 non-retina display. Took out the disk drive and put in my own SSD and RAM. Does everything I want it to do without the slightest complaint. All told I probably paid ~$700 less for a comparably powerful machine with 10x the internal storage of a late model MBP retina, albeit heavier and with a slightly inferior display.
Next time I need to upgrade I'm with you - it's just too painful to knowingly buy into an ecosystem where upgrades and repairs feel like unabashed extortion.
Obviously there's a very large target market of folks that just want their tech to work and will happily drop a few hundred bucks each time they need to upgrade or repair. But it's hard to go back once you've opened up your computer and seen how cheap/easy it is to replace some of these extremely modular components. I imagine my mindset will change as I get older and have less time/more disposable income.