Can you separate your requirements into "modern day stuff" and "legacy stuff"? I kind of upgrade OS X when I absolutely must, and it doesn't take long to hit some threshold where things just start falling apart around you if you don't move forward at least one notch. But, that's entirely dependent on what you need to do with the box.

If you're looking at 10.10, you're already more or less in modern land, as far as I'm concerned. I run 10.13 for my daily needs, as that's about as far behind as I can be and still be considered worthy of the Internet's time. I am gradually incrementing the OS on my mom's poor MacBook that she's had since they still had optical drives, because all the certificate stores are expired and she can't even browse read-only websites since every #%&$ thing has to be HTTPS these days.

OTOH, if I had some stable versions of apps that would run on Snow Leopard, I wouldn't hesitate to stay put. Just not on my daily driver. It's easier for me to give in and have one computer where I let the powers that be do what they will, than to struggle trying to convince the entire world it should still be supporting OSes that I happen to like better. That an option for you?

For SIP, you can basically disable it with a reboot to recovery partition - go to terminal, run csrutil disable. Reboot. Voila.
For running third party apps without the Gatekeeper nagging you every time, just run on terminal sudo spctl --master-disable and have fun.

SirNickity wrote on 2020-01-23, 19:24:

Can you separate your requirements into "modern day stuff" and "legacy stuff"? I kind of upgrade OS X when I absolutely must, and it doesn't take long to hit some threshold where things just start falling apart around you if you don't move forward at least one notch. But, that's entirely dependent on what you need to do with the box.

Not super easily actually... I'm in the uncomfortable spot where everything I use MacOS for is just old enough to be "unsupported" but not enough to be easily emulated or for workarounds to exist. Basically my entire suite of Mac software aside from browsers is "legacy stuff" by some people's definitions.

I ended up going with 10.11. I've already hit a few snags like this very specific SDL2 bug I had to work around yesterday, but for the most part it seems to run my stuff. I discovered Photoshop/Illustrator CS6, which I use all the time, never officially supported post-10.10 and you're supposed to move on to the "Cloud" suite. Well, no thanks. I bodged them enough that they work on 10.11, although who knows how many future versions that'd work for.

I have enough 32-bit software (which will never be updated) that there's no point in even having a MacOS machine if it just runs Catalina. Then I may as well just use Linux since it doesn't run my Mac software either. 😜 I have a couple of white (C2D) Mac Minis running Mavericks & Snow Leopard if I need them.

The whole 'rolling treadmill' model of computing just ticks me off... I know Apple have gone all-in on disposability and forced obsolescence, but it really annoys me how many of the prominent developers for their platform are taking that at face value and following suit. I'm not in the Apple ecosystem for the long haul anyway, I prefer to run Linux for bleeding-edge up-to-date computing.

At least now I get modern browsers, working ad blockers, Steam, spectre/meltdown patches, updated ownCloud, and I just don't have to feel quite as sketched out about using it for daily browsing. I probably could have gotten away with 10.12 or 10.13, but any of these are basically a stopgap.

Bruninho wrote on 2020-01-23, 20:51:

For SIP, you can basically disable it with a reboot to recovery partition - go to terminal, run csrutil disable. Reboot. Voila.
For running third party apps without the Gatekeeper nagging you every time, just run on terminal sudo spctl --master-disable and have fun.

Thanks for that! TBH I haven't found a reason to disable SIP yet so I think I'll keep that in my toolbox for when it's really needed. I thought it would interfere with Homebrew or block editing the hosts file, but it didn't.

xjas wrote on 2020-01-23, 23:43:

The whole 'rolling treadmill' model of computing just ticks me off... I know Apple have gone all-in on disposability and forced obsolescence, but it really annoys me how many of the prominent developers for their platform are taking that at face value and following suit.

Me too. I mean, technically I get it -- from a support perspective, legacy really really sucks. If you have the ability to put a finite window on support, it's only sensible to do so. I've been on the other side of that equation enough to see the burden it puts on limited resources.

What I don't like is how changes to the UI and features of the OS get taken away in exchange for keeping up with security and driver updates. If Windows 3.1's Program Manager is my cup of tea, what harm is it if I don't launch my apps with a Start menu? Bit of an exaggeration but, as an actual example, I still like iOS 6's aesthetic better than the "everything is white and that's clearly a button because... there's a word there" of modern mobile UIs. But... want to use modern hardware and be able to use websites? No choice then. Prepare to tap and swipe randomly to figure out what it does.

The children with short attention spans have taken over.