Rear Shock Settings
As for your question - My bike ('04 883 XL) was set to the factory setting when I bought it used from a guy here in Tx. I put about 1000 miles on it with the stock setting until I rode 2-up for the first time with my wife.
After that first 2-up ride set to the factory setting (combined weight of approx 330lbs-350lbs) I purchased the spanner wrench and clicked it up one notch (middle) bc of bottoming out every once in a while.
That did the trick for 2-up riding (no bottoming out) and I haven't had any problems whatsoever riding solo on that setting either, so I've left it at that. I think the middle setting on the 3-notch shocks is just about right for the average weight and rider, although I know a few people who set theirs up all of the way, and they weigh about as much as I do (190-200 depending on if the weekday or weekend.

Oh yeah, don't forget to put more air in the back tire if riding 2-up! Check your manual if you have any questions.
Nice bike man - I'm jealous!
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