I have mixed views on this. I bought a used 05 Sportster last year. Less than 1900 miles, but already out of warranty. Battery died and could not be recharged, so bought a new battery. Although it already had a windshield and a good after market seat, I added, crash bars, sissy bar, detachable mounts and passenger footpegs. Long cold winter did not ride much. Sportster was okay but, I really did not like it. I looked at lots of used bikes around here and everyone was asking to much for them. They expected to recoup their add on money, and many of the add-ons did not suit my taste. (Skulls, very loud pipes etc, flames etc......)

So I bought a new 08 Street Bob. Never regretted. First of all the six gear reduces the engine rpm on the highway, it has a built in clutch reducer so even at a long light I never put it back in neutral. It has power out the ***. Of course I bought a new detachable windshield, riders pegs, a Sundowner seat, detachable sissy bar mounts, still looking for a cool but functional sissy bar, and having a set of custom crash bars made. I really dislike the look of the standard Harley add-on and the Linbar which I like is expensive and looks out of place on this bike. Of course I have payments, but will double pay and pay every two weeks so I get rid of the loan about two years early and save a lot of interest. I love the 08 and the difference betwen 12, 14K does not seem like that much to me.

I'm sure you will be happy with the 06 also. If you are not running synethic oil, switch at your first change. It really keeps the bike cooler and reduces engine wear.. I may add the Harley external oil cooler depending on how the bike does here in Seoul this summer.

Good luck, don't forget to spend some money on safety. I am amazed at all the folks who max out the gadgets, and then wear a skid lid, light jacket and blue jeans. I have seen a few people take some nasty spills and the ones with saftey gear on got there money back on there first spill by saved medical bills, not to mention pain andlost work time. Full face helmet, a jacket with elbow ,shoulder pads, forearm guards a good set of leather pants with knee guards, and at least a set of ankle high boots made for a bike. Almost knee high is better. It can be uncomfortable, but compared to stitches, road rash, andyour teeth on the concrete etc...... well worth it.

Ride safe.

 

Absolutely not! You will be geting an OBSOLETE MODEL. Do not buy it! It is fair bit cheaper but the bike has depreciated for a reason - obsolete motor, hardly any warranty left, other more subtle changes from 06 to 08 modeland so on.

Unless you can find a good 2nd hand 07 or 08 model, buy a brand new one. Don't be svayed but a bunch of 06 model owners proclaiming how great their bike is. (and it was great back in 06). The decision should be made on bike's merit alone and with 06 you won't be getting value despite lower price.

By the way boyz, this wasn't intended to offend any 06 model owners here.

Cheers
Vlad
08 SB

 

None taken but part of merit is price & as far as I can tell, there's nothing wrong with my '06. Nothing. Got it for about $4500 less than new with about $1000 in mods (all of which I would have done).

 

get the 96" Bob, if you can, if money really is an issue then fair enough. But the 96" is the way to go.

- pete

 

I disagree 66cruiser.
IMHO the brand new 96" engine, 6 speed transmission and heaps of other changes, all coupled with new full term warranty worth every penny.
Afterall, the two up accessories can be purchased 2nd hand and he can select exactly what he wants.

Well of course, all of this is true providing you can afford the extra money for a brand new bike.
If budget is of strict concern, then 06 model is perfect fit.

 

I'm biased, as I have an '06 FXDBI. I bought it used a year and half ago from a family friend that has the financial ability to buy a new bike every year. The warranty transferred, and I've had no problems with it.

My advice would be to buy what you are comfortable with. The 88 c.i. with the 6 speed is a great bike. Yeah, they phased out that motor and went to something larger. It's still got more than enough power to keep you happy. Take a long look around the forums and see what everyone has done with their bikes. Decide what look, style, and feel you want and let that guide you. With good credit, you can generally get better financing with a new bike over a used one. Take that monthly payment into consideration. Either way, I think you'll be happy.

 

I would think that the EPA was the main reason for the increase to 96" (in Harleys efforts to comply with the new Federal EPA regulations), so I wouldn't be to concerned with getting an obsolete motor if I were you (even if obsolete is spelled out in caps). As for the six speed, I was fairly certain that the 06 came with
a six speed.You should be OK with either bike.

 

06, for 11 would be good, but so would as you say a later 90's model fatboy or heritage.
I ride mostly 2 up, and my 99 is just fine.
It is an evo too, with some slight mods.

 

The six speed trans makes a big difference that is being overlooked by many here. I'd get the new one and then pick my own riding setup.....

 

the '06 has the 6 speed... mine does anyway.