Hard to say, upgrade means going to a junior base which are almost universally high COL areas and you'd need to either move there or rent a crash pad for several months to several years until you can go back.
In my case, I'm lucky enough to have 0 ex-wives and no kids to put through college so I'm in a comfortable position money wise. It would take a pretty big chunk of money for me to take the hastle to upgrade until I could hold my base.
As a pilot the problem with upgrading early is seniority dictates QOL. A junior captain needs to work a junior base, fly a junior plane, and get whatever crappy trips are left in the schedule. That means that a senior First Officer would have to move or commute to a new city until they build enough seniority to go back to where they want to live all while working the worst schedule, or even worse sitting on reserve. Absolutely not worth the pay bump when you can wait a little longer and not have to deal with all that.
The gist of it is that they are making The Making of Karateka. Which appears to be basically the same thing as a director commentary for a movie but a game. You can play different versions and jump into the game during recorded bits.
I wanted to host a Minecraft server for some friends, so I got cobbled together a PC out of some spare parts and put Ubuntu server on it. Over time I added an emby server and tools to get media for the emby server and that was good for a few years. Then I moved and had some more space and fell way down the rabbit hole of used enterprise gear.
One of the basic differences between windows and Linux is that instead of C:\your_folder or D:\your_folder is that you mount drives as directories wherever you want in the filesystem. For example /home/username/documents could be on drive A while /home/username/games could be on drive B or even on a remote server. It's actually pretty common to put the entire /home directory on a separate drive which makes reinstalling or changing the distro very easy.
So to answer your question, yes you can put your games wherever you want and they will run seamlessly. Wine can be pointed straight at an .exe. the only thing that gets a little weird is when you try and run programs remotely through a network share, but you can usually solve that with symlinks.
I have opnsense virtualized on a proxmox server with a couple of things that should hardly ever need restarts. It actually works pretty well because the host almost never needs a reboot and rebooting a vm is way faster than bare metal
Working in that industry, in a jet with seats for 8 non-crew passengers (in ~50% more space than a Lear 45) most flights have 2-4 passengers, 1 is common, 7-8 hardly ever. Also you need the 172 if you want trained pilots in your 787.