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if you can find a 2002 RG is decent shape that would be the bike to have. RGs are getting so popular where you are it may be difficult to find a good one at a decent price. Second choice would be 2003 EGC/Ultra/RG in the black and silver paint scheme; you can tell your boys your part of Raider nation.
It would be easy to convert a Ultra/EGC into a SG clone.
Watch out for the street car tracks and muni buses.
I have been in exactly your situation....from Sporty to needing a touring bike for travel with the wife.....bought a Road King and loved it-put almost 80k on it so far....but I have spent most of the last few years making it into a Electra Glide/Street Glide clone.....you will wish you had the radio and tour pack.....buy a EG or SG and you will be $$ ahead....just my $.02
It's very easy, and not too costly, to rent all of the bikes you are considering. Of course you will be riding a 2011 bike which will be entirely different from the pre 09s, but you will still get the basic idea as to the differences between the three you are considering. I did exactly that (tried RG, RK, and Ultra) and ended up with an Ultra and love it. It's the right bike for my needs, but I would be thrilled to have any of them. Point is, try before you buy.
Sidenote - Road Kings seem to be more readily available than the other two you want and at a lower price. In shopping around I've seen models as new as 2006 for 10.5 and it was a sweet bike. Try Jaxed/Mash (Google search it) to find a ton of bikes in your region without having to slog through all the different CL pages.
Once you get that Touring, you'll never ride the Sporty (even though they are nice bikes) again I'll bet.
As neveda72 said rent each one first. When you are done renting you will know which one is for you. At the price range you are looking this will help a lot because you will be prepared to buy.
The guys with the Road Glides tend to be passionate about them, but they're a love/hate type of bike.
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...... for least initial cost & max flexibility I don't think you'd go wrong w/an RK. As others have said, the King tours well & you can later install a detach fairing & have most of the best of all worlds ........ it won't be a Road Glide .... but it'll fersure get'cha further on down the road !
Like yourself i kept my Sporty 08 883R as its so much fun to ride, i also had a NightTrain but as the wife swapped jobs so was free to ride on the back of me most weekends plus trips to France every year i traded it for a Ultra Limited that is great for the 2 of us .
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