As a long time macOS developer and user I too went down this road and ended up pretty frustrated. Even when you get things working perfectly (tackling iCloud services, driver issues, custom boot options, etc...) you're left with an installation that feels static.
Updates are slower to roll-out to the hackintoshes, major OS upgrades can be quite a bit slower to come. This can include security fixes too.
I ended up installing Linux and never looked back. It turns out most of what I used on macOS was just the unix-like subsystem. Having Linux was just as good, if not better than being on macOS.
Of course this doesn't help if you're doing iOS development, or need to use Xcode. I've moved away, myself, but have talked to others who have used a Mac Mini as a build machine. You could also install OS X in a Virtual Machine under Linux and use it for development, which requires its own set of hacks but fewer.
Linux distributions I would recommend:
* Solus, I really like where this project is going and it's my daily driver now.
* Arch, allows/forces a truly custom setup, you end up learning a lot about your system, but might be too distracted with your system to get work done ;)
* Antergos, an Arch alternative w/ batteries included.
* elementary OS, it's the Linux distro made by the folks who loved macOS. It's beautiful and you might like it more than macOS itself.
Had Lion on my W520, worked pretty well, after having to change WiFi card to Apple compatible. GPU was Nvidia only. Couple of other minor niggles. Somewhere around Mavericks/Yosemite it became more trouble than it was worth.
Having seen announced machine, and the price, I'm going Linux for next laptop. Might try to get a mini from ebay.
Please don't discount the value of building your system the hard way, aka "the Arch way". The more duct tape there is, the more headache you'll have later IMO. I recommend you sit down with the wonderful Arch Wiki and build your system from scratch over anything else if it can be helped. And of course, contribute :)
Mostly shouldn't be good enough. With System76 (and for that matter, Zareason) you'll have zero worries during OS upgrades, and never ever have to think about drivers. The laptop will just work.
Perhaps this is less of a problem today, but at the time I made my first purchase from System76 (2012), the sudden absence of video and sound issues after every other system update came as a welcome relief.
To your point, how does NLP address grammatical differences/errors, colloquialisms or slang? In the context of personal assistants every implementation I've seen has required more unnatural-language given the status quo.
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