This is a tough topic. I've been a Mac tech in higher ed IT for 21 years, having first learned on Windows machines in the early '80s and Macs in the early '90s. As a visual person (photographer since 1974) I ended up gravitating toward the Mac and prefer it to this day.
I guess you can summarize by saying those of us who love the macOS are frustrated with the current hardware, and if we like the hardware, we are frustrated with the price. With Apple products you do indeed get a premier experience (except for the occasional keyboard issue and such, and maybe the OS itself it getting rushed and sloppy), but you pay the Apple Tax to participate.
Also, Apple does push the envelope in terms of moving forward with technology (tough love?). At this point none of us miss the floppy disk or CD/DVD drive, right? But the disappearance of everyday connection ports is a bit much, as is the obsoleting of still viable Apple hardware by new OS restrictions.
What to do? Many people say Apple's current offerings are underpowered and overpriced. The new Mac Pro (for Pro's only, it $eems) is certainly powerful, but $5-50+K, really? I suspect very few of us here will ever own one. So unless we are dealing with business write-offs, our realistic choices are more limited. The new Mac Mini (I have tested one with Maya and it seems to perform well) still gets poor reviews for its price/performance ratio. Otherwise it might be our go-to sweet spot.
Option 1:
Some of you mentioned preferring older Macs for onboard access to ports and perhaps better used pricing. BTW, you can run Mojave (and Catalina if you dare) on 2008 and newer Macs (Google "dosdude unsupported macs"). Just last evening I updated a Mojave installation with the latest Security/Safari update on a spare 2008 17" MacBook Pro. Even with only 4 gigs of RAM and an older small SSD installed, you'd think you were surfing the web on a current computer! Imaging apps are usable as well, though of course there will be speed issues there. So don't write off your older Macs yet.
Option 2:
Buy a used recent-model Mac (let someone else pay the Apple Tax). Enjoy that reliable Mac for the rest of its useful life.
Option 3:
Some of you mentioned using VMs above. I have a Snow Leopard VM on hand should the need arise, and routinely run Windows and Linux from my Mac this way (just because I can). If you dare you can run macOS from within Windows. So there is no need to lose all your 32-bit software, even on a newer mac with Catalina.
Option 4:
Build your own. This is common in the PC world. Mac users can take the Hackintosh route (for the near future at least) and get twice the performance for half the price, so long as you don't mind getting a bit geeky. I also have a triple-boot 2011 build Hackintosh for fun (Mojave, Win10 and Deepin Linux) that I actually end up needing to use for the odd task (recovering files from Linux-formatted NAS drives, etc.).
At this point, looking ahead to when I don't get toys at work and need something of my own better than the 2013 MacBook Air I use at home, I think I would choose the Hackintosh route. That way Win10 is there, Linux is there and macOS is there – on the upgradable hardware of my choice. Second option would be a used (current model) Mac Mini for the true "Apple experience" ;-)
