Using Classic Outlook on Windows for personal email, calendar, and contact management
Yeah, no, don't do that - you will definitely lose your history.
We've established that if you make changes in the Outlook web version (not the desktop one), you have the options of editing just the current event, this event and following ones, or all events in the series. This keeps your history of changes, and will sync to your desktop version with history intact.
One day Microsoft will see fit to make these options available in the desktop version as well, but I'm not holding my breath.
I now have my Outlook calendar open as a web tab and do all my bookings there. The rest of Outlook I use on my desktop version.
Cheers.