I actually set up wp supercache just last night, and it seems to be working quite well for me. Unfortunately, I can only use the caching algorithms from the original plugin, and not the newest ones, because the server my site is hosted on is missing one of the apache modules needed for the newer algorithms.
I found it was moderately easy to set up, though I definitely needed some help from the troubleshooting section of the plugins page. It took me about 15 minutes to get the plugin itself set up, and an hour in total if you count the time to install plugins to backup my database and to then actually backup the database and site beforehand. I definitely wanted to be able to restore the site if things didn't work out, since I've heard of a few people having some issues with the plugin that made their sites not work properly. This seems to be very rare though, and certainly hasn't been my experience. But hey, that's what the backups are for. And I really needed to get the ability to make backups easily anyway, since I really should back my site up more often just in case.
The backup did turn out to be useful once, when I messed up editing a file and saw my site was missing afterward. To be safe, anytime you modify a file, just check your site afterward and make sure it's still there, if it is, you can move on, otherwise, time to get your old file and then try again.
I might be able to say more about the plugin in a bit, for now, I want to see how things go for awhile before I heap too much praise or criticism on it. For now though, it's safe to say it's doing what it's supposed to, and might not be a bad idea if you need your site to be more efficient.
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