I have an '01 FXDWG but want to get an Ultra Classic. I want to get a new one but hate parting with that much cash. What model year would be a good choice for a used one?
2002 was a good year, still had the timken main bearing, forged flywheels, delphi FI and new swing arm. Good low mile examples can be found for a reasonable price as well. One just sold not far from me with 13k miles for around $10K.
If you want newer, up to 06 are pretty reasonable. Once you jump to the 96 and 6 speed, the prices jump a bit.