Stars Without Number is a fun system. Traveller can be a bit complex but the character generation is the best.

You need Windows installed first, set up your partitions, then install Linux. You could backup your data and then restore it. That’s the easiest way if you choose not to use a windows vm.

If it is cloud hosted then there is always a possibility. Programs like keypass run locally and are only in jeopardy once your system is compromised. The issue with keypass is implementing it for multiple users is probably a chore (never looked into it).

LTT isn’t making sure their info is correct. They also can’t be trusted to give stuff back.