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How is the overall Hackintosh user experience in 2021?

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Building a new hackintosh today means fossilising on it, with little to no prospect of upgrading
Some people Hackintosh to learn things... Not everyone has to be on the bleeding edge of technology. I still build hacks based on old 61 series motherboards, because they are cheap, and that is all I need them to do. I have a working Commodore64, Apple ][c, Apple ][e, Macintosh Classic II, many PPC macs, many Intel macs, and many Intel hacks. And some day, I will likely get some M-based macs, and likely someone will find a way to build hacks of them in the future. I don't mind fossilising.
 
I’m happy fossilising too!, hackintoshing isn’t about the destination, it’s about the journey!. Pretty sure there’s a whole thread about this somewhere. I’m not going to build a hack that would crush my M1 MBA. I’m going to build a hack because I want to learn something, I want to look at form factors and have fun along the way.
 
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Some people Hackintosh to learn things...
I fully agree with the learning experience (some of mine is summarised here), and do not mind fossilising on my Cascade Lake Xeons. But the OP was apparently seeking up-to-date hardware and is on a update cycle for his laptops that is relatively short, by the standards of Apple users. The OP may have good reasons for that; I had to warn him that, with Apple transitioning to its own chips, he could only do a one-shot of a hack, not on the latest Intel CPUs and with no realistic prospect of upgrading in four years.
But as long as one sticks to 10th gen and earlier the 2021 hackintoshing experience is certainly the best that ever was.
 
The last time I had a hackintosh must have been 10-12 years ago. I distinctly recall hardware support, and OS updates being a constant source of pain. Since then I've owned nothing but Apple laptops/iMacs, but have experienced significant hardware problems with each one within ~3 years. The latest of these has got me thinking about a hackintosh again, as I'm very tired of blowing $4500 CAD on the latest MacBook pro every 3 years.

My biggest concern is how much day to day headache I'll have to deal with to ensure things are not only working, but keep working. I do see there are some new installers of major OSX releases available, and seemingly lots of builds with full hardware support.

Is the current hackintosh environment a "set it and forget it" type of deal, or is there a semi/regular need for tinkering, fixing, etc.? What's the overall experience like? Any advice for the "safest" path towards a build that won't require me to constantly screw around and debug it?

I started about 9 years ago in the scene. It has improved tremendously. OpenCore really is a game changer. It's so easy to get a OS running compared to clover back then.

The most important part of having a Hackintosh is to buy compatible components. (Motherboard #1).

The craziest thing is that I have been running the same install. I believe it was Lion or Mountain Lion (Mavericks??). That same install has been upgraded all the way to Monterey now. The drive was cloned from HDD, to SSD and now to NVME. But I have never had to "re-install" the OS.
 
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