[ThePythonicCow]

Quicken is one of my concerns, but I’ve read online it can be done.

Not entirely. Older versions of Quicken work better in Linux based emulators such as WINE, but if you are a serious Quicken user, you really need to continue running a real Microsoft licensed Windows boot, either on a separate dedicated Windows PC, or by dual booting, or within a full Windows emulator such as VMWare.

[Still Thinking]

What the heck could Quicken be doing that would make it so finicky?? It’s a money management product, for God’s sake.