I bought my '02 new and it's never let me down. The only issue is the cam chain tensioners. As long as the motor has bnen taken care of, the '02s and teh TC88s are bullet-proof. Newer is not always better. Shinier, but not always better.

 

I have an '04 RK Classic loaded with extras.... Solid bike.... Not for sale!

 

I did what you are describing. I had a '09, sold it and for half the money got a mint '02! Loving life!

 

I wouldn't get rid of my carbed '05 for love or money.

 

My 04 EG has 91K on it and no end in sight. It's actually a 95" stage IV set up and I love it. I did replace cam chain tensioners at 58K, and at 89K I upgraded to the hydraulic set up. I absolutely would recommend a Tru-Trak or the equivalent. Swing arm steering sucks! I will never go back to carbs--I have an old shovelhead if I want to play with a carb.

 

05's can have tensioner issues and valve seal problems as has been mentioned. Mine is using quite a bit of oil now, and I'll eventually have to get that fixed. That'll just be a good excuse to do cams and a big bore kit. I have very little interest in trading for something newer...

 

..stay away from ANY injected Harley prior to 2002....you should be able to grab a nice RKing...oh..say 2002-05 for anywhere from $9500-$12,000 depending on extras, mileage, and condition...good luck, and don't feel bad...you are doing the responsible thing, and living within your means...something I wish our government had done a long time ago...instead, we are now F*CKED!

 

I love my 01 Ultra. A lot of people complain about the Magnetti-Marelli injection, but mine's been trouble free for 37000+ miles. It also has the forged crank and Timken bearings. Cam tensioners replaced at 13000 miles with gear drive cams and upgraded to a Fuelling oil pump and never looked back. Wouldn't sell it for any amount. ( Indy told me it's the best handling and running MM injected bike he's ever been on and wants first shot at it if i want to sell it, lol)

 

I love my '03. It had 2090 miles on it with a Stage 1 upgrade. Like the Power Band, and 5 speed is fine. I don't run over 80mph much, so I don't know if the 6 speed is better there.

My bike was traded in on a trike, which is a great reason, to trade in a good bike. If you are not in a hurry , why don't you ask your dealer (or several dealers by email) to keep an eye out for a cherry trade on a trike? I didn't get the warranty, but if you want peace of mind, you could get that.
Good Luck

 

I don't get trikes. You drive them, but ride a bike. I fell in love with riding as a tot.
Still, each to their own, and the needs of the injured.