I have an 06 fatboy and Yea Ill say it he's a chrome *****!!!

 

I too just got a FB after 30 years without a bike. I was concerned about the weight vs the 450 lb. bike I rode years back. But I have had no problems or concerns so far. FB is well-balanced and has a low center of gravity, very easy to maneuver (I'm 5'8").

 

You'll do fine with any year Fatty. As mentioned above, if you want the 96" and six speed you'll have to go '07 or newer. That being said, there's absolutely nothing wrong with the 88" and five speed either. You should have no problem finding many, many later models with very low mileage. They're all over the place. People buy bikes and they end up being garage queens. Nice 700 lb. bike with a low center of gravity. You'll be able to throw it around no problem in a matter of a couple of weeks. There's very few problems with most any soft-tails. They don't have all of the electronics that can go wrong like you do with baggers. You'll do fine and be able to find a good bike with low miles for a good price, it's a buyer's market out there.