It sounds like the clutch lifter at the case is adjusted a little too tight. This lets it go over-center when pulled in, then it won't slide back. Try adjusting it fully slack at the case, then turn toward tight, then back off a bit and set the bolt. Many of those lifters now have a notch worn into the lifting screw groove, which can make for a sticky spot, too. If you take it out of the case and clean the parts well, you'll see it: filing away the ridges of the lips of that groove will restore nice operation again.
If the clutch was greased on schedule, this happens around 40k miles. If never greased at all, like most 500/550 bikes, you're lucky to reach 20k miles before this happens.