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#21
In this test I went from XP to 10 using all versions in between, meaning that I went from Vista to 10 via both 7 and 8. However, the 8 was only for test purposes, you can skip that; the Windows 7 is necessary as Vista can only be in-place upgraded to Windows 7, not to 8 or 10, and then 7 can be in-place upgraded to 10 skipping 8.
All compatible software, settings and your personal data will be intact whatever valid install media you use for in-place upgrade.
Short answer to your question: yes.