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Ah man this really is tough, your post details a lot of what’s on my mind, but I think ultimately these three win out;
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Minecraft - especially given the fact that we have access to the entire modding sphere, it’s just plain silly how much creativity has been poured into this, and the game is pure nostalgia for me. I could get lost in it for aeons.
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Dwarf fortress - wins out to CDDA because I’m a strategy nerd. What has ended up killing me in the past with this game is how much time it takes, but on a deserted Island? Well, time isn’t an issue.
The last one is perhaps the most difficult, but assuming that I have access to a sufficiently high-end pc, I’d want KoboldAI (United) with all currently available local models downloaded. This is only borderline a “game”, but I am able to modify the software, and the possibilities are simply endless for creativity. It’d definitely ease up the loneliness a fair bit.
Those 5 requirements are not small things, but as a (relatively) recent linux migrant, here’s my take.
Keep using iTunes (but use the windows version) - through wine. You get to keep all your stuff as is for now with the possibility of migrating to another service in the future.
See above, stick with your current device, keep using iTunes for now.
If it’s for private stuff LibreOffice suite does just fine though + the thunderbird email client. If it’s for work you should probably have a work device, but there is also winapps for linux, which isn’t official by microsoft, so it might be a bit funky.
Maybe try out proton if you want something trustworthy to back up your photos. They’ve recently added a service for that. Costs a subscription though.
Keep using evernote. There’s a linux client.
Obviously there will be hickups, and things’d be a lot more smooth if you were willing to make some adjustments, but this is perfectly doable.