I don't think I lost a single hack, and I might have gained a couple.
I have had very positive experiences upgrading except one time.
I disable all plug ins, upload the files, run the script, and one by one reenable the hacks. If the hack has a up to date equivelant I install that instead. I check before I upgrade though, and completely uninstall those that do. It's really quite simple and worth it in my opinion.
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