There are some REAL bargains out there on "older" bikes. I bought my '00 FLHT in 2004... at the time I could have kept my shovel and bought the '00, or sold the shovel, added all that money to what the '00 cost, and bought a new Classic. I kept the shovel and added the used FLHT (had a whopping 7000 miles on it when i got it)
Made sense then, still makes sense
The new ones definitely have some seriously nice upgrades from my bike, ones I'd really like to have: 6 gallon tank, brembos/abs, better frame, bigger back tire, 6 speed, cruise.
But my 95" '00 only has 25,000 miles on it, runs great, has decent power, and is a great 2 up touring machine. As much as I'd like a newer one, I don't need one, and I don't need any debt.