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The further back you go into gaming history, the more likely it will be that you're going to have to interact with the command line, wine, reading documentation, and generally muddling your way through. There are a few programs out there that try to streamline this process, Lutris and its install scripts being one, but even this can be very tempermental and involve a willingness to test things out and mess around with wine components/overrides. As others have indicated, go after the low hanging fruit first, which is EmuDeck and console emulation. That should keep you busy for a while. As you are having a great time with that, start playing around with Lutris, Bottles, and DOSBox-Staging (mainline DOSBox hasn't had a release in a while). There are a tonne of videos out there covering these projects, but documentation is honestly your best friend here. If you need a good video source, Gardiner Bryant and GamingOnLinux make decent videos about each of these projects. Have Fun!
The further back you go into gaming history, the more likely it will be that you're going to have to interact with the command line, wine, reading documentation, and generally muddling your way through. There are a few programs out there that try to streamline this process, Lutris and its install scripts being one, but even this can be very tempermental and involve a willingness to test things out and mess around with wine components/overrides. As others have indicated, go after the low hanging fruit first, which is EmuDeck and console emulation. That should keep you busy for a while. As you are having a great time with that, start playing around with Lutris, Bottles, and DOSBox-Staging (mainline DOSBox hasn't had a release in a while). There are a tonne of videos out there covering these projects, but documentation is honestly your best friend here. If you need a good video source, Gardiner Bryant and GamingOnLinux make decent videos about each of these projects. Have Fun!