I would go with an '08 and up if you can afford it. They are all good and all have a few things that were wrong but most are fixed by now. The '06 and down had tensioner issues

 

I had a 07-96ci-6 Speed and absolutely loved it. No problems what so ever.......Here is a pic

 

I am with you...think the link chain fixed in 07 on the big cruisers was not fixed till 08 on Softails. Bobback, be real careful and check it out closely. People screw these bike up royally not knowing what they are doing and get rid of them..If you are not familiar, pay a good mechanic to check it out..indepently of a dealer if you get it from one.

 

+ 1 for the carb. Love the idle !

 

Own an 04,love it.
If you are a fan of the wider rear tire you may wanna go with 07 or later.
As others stated,bigger motor and 6 speed on later years.
Take your time and pick one you love

 

Stick with 07 and up. The 96 ci and 6 speed was the selling point for me after riding one. I have an 07 and have not had an issue one. They fixed the timing chain tensioners in 07 also.

 

Is post #11 a Fat Boy?

tonetls...can't see your pics as I'm just a basic member.

 

It depends on how mechanically inclined you are. I picked up a 2000 with 13.5k miles for a hair under 5 g's. That being said Chain drive cams to negate the tensioner issues- $1000, new rotor disk $100, solo seat-$50, front fender-$150, used Mikuni carb-$75 and this downtime for winter, 96 bolt on with ported heads-$1100, so without incidentals like swingarm bag-$125, and detachable windshield-$300. I am already up to $7k and will likely repaint when I upgrade the engine so my total cost spread out will be a hair under $9k. This is on a 14 year old bike I will never see the money I spent if I sell it. The upside is it has been a labor of love and right now just cammed up with gear drive .510's with a stage one and an aftermarket timing system I keep up with the stock and stage 1 96's without breaking a sweat. It keeps me busy and It is great watching the bike come together. In all honesty though if I had the cash, I would have been happy to slap down $12k and walk away with a nice almost finished 2009 0r '10 which are out there in pretty decent shape with a 96 or 103 c.i. The deals are there. A lot of RUBs buy them and either lose interest or quit after a near miss and want the thing out of their garage.
You can see my avatar what it was when I bought it and the pic below is about 3/4 way through the mods.

 

here's a few just jumping on cycle trader that struck a nerve

http://www.cycletrader.com/listing/2...-Boy-110628594

http://www.cycletrader.com/listing/2...-Boy-106752479

http://www.cycletrader.com/listing/2...-Boy-112084950

http://www.cycletrader.com/listing/2...-Boy-111158924

http://www.cycletrader.com/listing/2...-Boy-112145290

all these have low or super low miles and asking price is right in your budget

 

Appreciate the feedback/advice...thx!