Judy wants to be able to access her data from one computer to another. Leo says that's called synchronization and it's very doable, but it requires internet access. There are third party companies like DropBox and OneDrive that will do this, as will GoogleDrive. But there are other ways. Leo is currently using SyncThing, which is open source and free. Leo says that OneDrive may be the best option because you can tell it what to sync and where. But you need to know where that data is in order to do it. Judy may have issues with Quickbooks because of how they save the data, but it's doable with some research. Quickbooks has its own cloud sync as well. So that may be the best option.
What's a good, light laptop with a good keyboard? Leo likes the Dell XPS13. The Lenovo Thinkpad is also good. She also needs a scanner/printer that's mobile. Leo says that Epson (a sponsor of the TWiT network) makes a good portable scanner for $100. Plugs in via USB.