Trade?
I found a guy looking to trade his 87 Softail standard for a sporty 883 hugger. I happen to have a 94. The softy has 33,xxx miles on it and has tins ready for paint right now and needs a primary gasket. My sporty needs the o ring that goes to the end of the clutch cable and that's it. The sporty has under 13,000 miles. Is this a good trade?
Agreed, trade if the bike is in good shape. I would always look to trade up for a bigger bike, again if it's worth it. The thing is though, you know what you have in the Sportster. With the 87 you only know what this guy tells you.
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When looking for a bike I was told not to go any older than a 1990. But I dont really know much about Harleys at all. I guess look at it like any bike you are considering buying. Definately take it for a ride. Run her through the gears, test out those brakes, feel how she rides, use all the lights. If she goes good, grab it.
Issues are always gonna come up with an older bike, but if you are starting with a solid foundation, just deal with them as they arise.
Good luck

Issues are always gonna come up with an older bike, but if you are starting with a solid foundation, just deal with them as they arise.
Good luck
FYI I picked up a 93 softail that had unpainted after market tanks an a messed up front fender for $4100 an have a nice looking bike for under 5K so you should be able to sell your sporty an find an evo softy for a deal
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