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It all depends what you are after. 2007 is when they put a fat tire on the rear. I like my 2002 just fine. 2000 and up will all be with the TC88 motor, 2007 and up is the TC96 motor and fat rear tire and 6 speed gear box.
Depends on what you can afford and what you can find. I called shops from northern Oklahoma and down to Houston looking for a Fat Boy back when I got mine. Most dealers said they didn't have one and only had one on order for this winter. When I walked into the dealer in Grand Prairie they had just unloaded 2 red Fatties that day. I walked outside and looked them over, then said lets talk numbers.
Our Fort Worth dealer had a few 08's last time I was there. They don't want to sell them for the price you can buy an 09, so I told them to keep their bike and went to buy an 09. Now I ride mine up to their front door and go in and walk around. I still have the tag frame on there from Longhorn in Grand Prairie, so I like to park it up front and let the salesmen see it.
You can look for used if that's what ya like. After getting mine I'm glad I got the 6 spd and the 200 rear tire. It's the kind of mods some people pay lots of money for later.
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