Practiced on a test server for a week....till I got it down to about 2 hours
then installed a mirror site on the same domain and did the upgrade at 2am
finished around 4:30am and renamed the mirror to the original. very few issues other than a few broken paths......and some of the old templates had to be manually edited to get a few of the 3.5.4 features working
only lost a handfull of posts and no one was the wiser
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