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I was in a similar situation last year. I had a 2007 superglide ended up trading for an 08 streetglide, best desicion ever. you will not go wrong with the flhx.
When you get your bike sold , buy your buddies bike. Don't complicate things by throwing the 08 vs 09 debate into the deal, don't be that guy. Paralysis by analysis is killing most people from getting anything done, you will love the SG and be riding while the other guy's are still on their slide rulers trying to figure out resale, residual value new vs used and so forth. I am biased toward the 08 SG , go figure!
You will love the SG. Sure, you will hear all of the talk about going to the 09, but the 08 will be so far above your Superglide it will absolutely amaze you. Enjoy!!!
I jumped over to the dark side from a 04 superglide to a 08 street glide. I loved the hell out of that bike but as soon as I left the stealer's parking lot I forgot all about that Dyna. Now with that said my girl just bought a 09 street and I have to say the difference is amazing between the 08 and the 09 but mine is still faster cause it's black.
I was curious to find out more about what you refer about the amazing difference between the 08 and the 09.
1) You'll have to fight off all the hot chicks that SG's attract
2) You won't get anything done at home anymore since SG's are such a joy to ride - long trip or short
3) Have to make tough decisions about what music to listen to - radio, CD's, etc.
4) You'll spend more money filling up that 6 gallon tank
5) You'll have to decide when to use that pesky sixth gear
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