In all honesty, it's probably only worth $3500. I was going to ask $4500 and see what I got. And thats probably a high estimate. I just don't want to get into a boat that's going to depreciate by half when I want to sell in a couple of years when I'm ready to upgrade. Mainly I'm looking to see how people really feel about the Catalina 25.
Ok, now we are getting somewhere. Keep in mind it is human nature to over value our possessions, so I will say your bike is likely worth 3000 (not an insult, just going by numbers for quick sale) Catalina 25's around here in the north east sell for around $2500 - 3000 if you want to sell quickly, unless they are mint, with new outboard, and new sails. So likely they it is not a bad trade for both parties. No one would be getting a smoking hot deal or anything for either party. Catalina is a great boat to learn on, and you could even likely do some coastal cruising if you are ok with minimal comforts. My understanding of California cruising though is there is not a lot of "coastal" meaning being able to duck into a port if it gets ugly. Not sure if it will fit your needs. For live aboard I would at least look for standing head room and a real head. Personally I would want pressure hot and cold water but I want to live the life! I would think living on a Catalina 25 would be better than being homeless but not a huge jump. Think living in a mini van with a porta-potty in the back.
The thing to understand is that major boat parts are expensive to replace. So you want to make sure the sails are in good shape, say less then 8 years old. Rigging should not be more than 10 years old if you expect it to have much life left. Both of those are going to be well over a boat buck ($1000) to replace with new, and could be a couple. New outboard will be a couple of grand.
By the way I agree I think the 883 is a great bike, but my ideal bike is a BMW R65 so what do I know? Just not a lot of demand for either, so prices can be depressingly low.