I have tons of motorcycle magazines. While getting our Christmas decorations I found the December, 2010 issue of Cycle World. On page 47, Allan Girdler has a single page article titled Sportster Buyer's Guide. He has several 50's and 60's Sportsters, so you have to take his advice with a grain of salt.
The older Sportsters are for collectors. They are "rough and raucous fun", but "it 'takes dedication to make one a daily rider." For value, he likes the early EVO's (1986-1990).
"The newer models are expensive, often too complicated for the home mechanic. Worst of all, they are 50-plus pounds heavier than the earlier EVO XLs and performance is no better than adequate." On his post-90 Sportster, his belt drive broke once and since the Sportster is a torque motor, he says the fifth gear is marketing.
I remember when the EVO Harley Sportster first came out, Nick Ienatsch made a XLCR (1977-79 Harley Cafe Racer) out of it. It was beautiful and way outperformed the original. I saw several 86-90 Sportsters on CL for $2500.
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