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First and foremost, you don't have to stay on the distro you start with. You can try a few, spend a week running it, and then reinstall with something else. Distro hopping is the process if changing distro frequently and is in my opinion a very useful start for learning Linux.
Second, Ubuntu is a perfectly fine distro. I don't like or use it, but I also don't really like chocolate but love licorice, it really is a matter of preference. If you never try it you will never know if it is good for you.
I think the best path would be to either use virtual machines on your main system or try a few distros out on your Windows 8 machine. I would recommend trying a few of the most popular distros including Ubuntu, Mint, Fedora, EndeavourOS, elementary, and maybe Pop!OS. That should cover most of the different desktop environments, packaging systems, and overall design methodologies and give you a really rounded sense of what is out there. It should also give you opportunities to have things break a little and for you to try to solve those problems. I find that different distros present failures a little differently and their solutions also work differently, so finding one that works well for you is key.
I personally ended up switching from a vanilla Arch install to EndeavourOS a year or two ago because it had great sane defaults, good packaging, and fantastic performance. The clarity of the logs was better in my mind than what was available in Ubuntu based distros and while I love Arch it was a bit too demanding of my time to figure out each and every choice of package. EndeavourOS gave me good solid defaults and reduced my work load.
Just remember, your choice of distro is like your choice of underwear. You have to wear it, make it comfortable for you and your junk, not for someone else's.
The sound of virtual machines on my main doesn't sit well with me. If I do something and brick my main laptop I'm fucked and I can't replace it and some of the programs I use won't run at all/run well on my old Windows 8 machine because it doesn't have the processing power. (I got a gaming laptop so I could have the video processing I needed for video editors to not take a day to render a 15min video on Windows 10, never mind and older Windows 8 laptop. sigh) Experimentation and tech FAFO'ing will happen on the Windows 8! lol
I've seen Pop!OS come up in a few comments here, so if I don't end up liking Mint maybe I'll try that one out next. :)
I would ask how many times you have bricked your Windows machines in the past? That said, if you did stop it from booting it would be the same as it not booting a native Linux install.
That said, I would recommend installing first on the older machine. New life for that machine will feel good and it is very low risk. Once you have done a few installs and not botched anything too badly you could give it a go on your new machine. I find the performance boost from using Linux over Window is enough to out weight significant hardware differences most of the time.
A Windows computer I had got massively fucked once like, 15ish years ago. No idea what happened. No new downloads or installs, I hadn't done anything different from any computer I've had before or since, just one day it stopped and it wasn't even that old, two years tops. Not a custom build, straight outta the box from Best Buy (maybe even Future Shop it was so long ago). My friend couldn't tell me what happened when they figured out how to get it at least booting up again. Only time it's happened. It was weeeeeeeiiiiird.
Glad to know about the performance boost. :)
Yeah, I've had bad random things happen with tech, only with systems that are closed though. When they are more open you can get logs, see what is happening, and eventually modify things until they work again. I had a phone that just wouldn't stay online for more than 5 minutes if the screen turned off. Screen on, internet working just fine. Screen off for 4 minutes, perfectly happy most of the time. Then suddenly around 5 minutes it would just die. It was running Android so I could see some stuff but I simply couldn't get the information I needed to figure it out. Linux is much more forgiving with logs and such giving actual error messages which with a simple copy paste can get you to a reasonable next step.