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I have hundreds of Wordpress installs and this is what is working for me:
Install InfiniteWP on a cheap ass vps or shared account (preferably any hosting account that doesn't have all your Wordpress installs on it) and setup all your blogs on it then it's really easy to update. I can't believe I went this long without using it..it makes updating so much less time consuming.
My only problem is when I first started I didn't use child themes so I have to be really careful updating themes so they don't lose any custom coding I have on them.
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