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Even without the thought of trading the 08 for an 09 SG, I think I would make the deal. Trading up 2 years and 20000 or so less miles would be hard to pass up.
OK, I've got a guy wanting to trade me his 08 electra glide classic w/1500 miles on it, 2 seats, 2 windsheilds, quick detach tour pack, for my 06 Street glide with Lsr 2/1 exhaust, mustang seat, screaming eagle heavy breather, 21 front 18 rear, 23,000 miles on it, wants to trade even. Just wondering what you would do.
Does he owe anything on it? Do you like riding solo most of the time or do you ride 2 up ? This is like the commercial, Butter or Parkay!
If it's a straight across deal, I'd say take it. You can put the 21X18 setup on it, and you've got a two year newer bike with much less mileage. Does he take good care of it, is there any mechanical issues, does the bike run strong, and have you ridden it? If all those things are good to go, I don't see how you can lose. Mileage difference and year difference makes a strong case for the trade. And you've got everything you need to convert it to a SG except a smooth front fender if you decide you want to. What's the downside?