I've had no trouble when I've moved to a newer version of Quicken (both on Macs). They just ask you if you want to import data from an older version. I'm sure there's a way to import data from a PC version.
I followed their advice and that of Intuit. Registers transferred OK except for the fact that there must be a bunch of double entries because the bottom lines don't agree. But intuit did warn of that. Seems to be a common problem when going from windoze to mac.
Fortunately both of my machines are still working and it'll be simple to set the monitors side by side to compare registers. Oh, well. It only needs to be done once.
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