go '08. I bought an '03 nightrain a year ago and after some long painful rides bringing up the rear, I just upped to an '08 fatboy (w/16" apes now!!)... Won't happen again.
You're gonna eventually want that bigger motor and transmission, and might as well bite it now while you can finance it or negotiate good (especially considering the economy, no one is buying anything), as opposed to coughing up a couple G's out of your pocket after sturgis (or however long it takes you to get tired of following your buddies).
Also, the 07+ fatboys are miles above the old ones with the fatter tires and advances in balance and suspension, new is the way to go... in my own humble opinion.

 

+1 for 07 and newer

 

I love my '08, and so far, added another $3,600+ in accessories and mods (stage 1).

As others have said, its all about where your budget is and what your mind's eye has in store for what you want.

A less expensive, older model, will give you money for paint, wheels, etc. A newer model will give you MoCo's latest technology and possibly less money to spend for changes.

The dealers have some pretty sweet deals right now, great interest rates and other incentives.

It's all about YOUR budget. Glad to hear that you decided on a Fatboy.

[sm=icon_cheers.gif]

 

Well 07-08 comes with a little bit of meat on the back end also. What does a 200 kit cost to upgrade?

Plus my six speed on the highway is NICE Harley should have done that years ago.

 

Good Morning hdokie...

Any Fat Boy will bea great choice for your ride, but I tend to lean to the newer models. The 96 + 6 is a huge deal when comparing the older to the newer. Granted...being the owner of an '07 I'm a little biased in my opinion, but I personally would spend the initial $$$ up front and then save to dress it up.

But either way...having converted from sport bikes you'll be a happy camper with your HD choice! Welcome brother!

Steve

 

I was in the same boat a week ago. I was ready to buy a 2006 used Fat Boy with low miles. I decided to go look at a new one and I fell in love with it. The wider rear tire and fender is bad ***. I have had mine for about a week now and I have no regrets. I am so glad I went with a 2008. I love my new Harley. I know I made the right choice.

 

Go with an '08, or if you find a steal, low mileagefrom 2000 to 2006.

 

What tlb said....an 05 with a 95 kit will outdo an 07/08 anyday...

 

I agree with jeffbarb17and a few others...$3500 will get youthe big bore and a bit of chrome. I would opt for the 05 and do the 95" big bore. It just depends on how bad you want the wide back tire. I have a TC88 with just510 gear driven cams and the standard exhuast and breather upgrades and there isn't aTC96 without major upgradesthat will touch it.

 

I bought an 06 Fat Boy and installed the 95" kit with cams and heads. All this for a lot less than a new bike. However, if you like 08s better there is nothing wrong with that either.