I wouldn't worry so much about iTerm and would start working harder on those issues that are preventing you from updating.
I wouldn't worry so much about iTerm and would start working harder on those issues that are preventing you from updating.
However, I don't know of good answers to the issues that prevent me from updating.
For most of my work, Linux is used in VMs and remotely (Linux in a VM on a Macbook uses much less power than Linux running natively, and side-swiping between Linux and Mac is really great). But I don't use the Linux GUI much. My open windows are virtually all iTerm2 or Firefox, and almost everything that isn't a GUI is on a Linux command line somewhere.
So there isn't a strong imperative to update the host OS of my laptop.
However, what I lose from updating is significant. There are things that can't be done with much more recent MacOS, or which work significantly differently, or where the bugs have changed so introducing risks (SMBFS random file deletion, thanks Apple!). And Apple has a very annoying habit of making it next to impossible to build things for old devices on new Macs. (Unlike, say, Linux, where you can at least cross-compile or use chroot/containers to run old build systems.)
The real answer for the things I want to do is to buy a new machine and keep the old one around to support older devices that it is currently doing.
But I'm in the same dilemma as other people hoping for a great new Macbook Pro (after 2015) to come on the market at a sensible price some day. Besides, they have become very expensive, and my current one still works very well.
So in practice, I don't have much in the way of security risks (Firefox and Linux are updated after all), but iTerm2 is probably the only vulnerable tool I use daily on the Mac side which is exposed to data from the net.
And so it made sense to ask, just in case. I completely respect the author's reply.
If you're running a version that is not receiving security updates, you remain vulnerable to vulnerabilities discovered (perhaps in later versions using same code) after the updates have ceased.
It's a complicated pro-contra decision, but in Apple's case it's an easy decision. They have abandoned all developer good will some years ago already.
Running current versions is rarely advisable. Just see the gcc-9 disaster.
(I wouldn't run Linux on bare metal on a Macbook Pro though, because I already did some experiments and found it used less battery to run Linux under VMware Fusion, than to run the same Linux bare metal on the same machine. Counterintuitive perhaps. Maybe even wrong :-) but that's what I found at the time.)
If it ever dies, I might just get another one.