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Another shovel chap here, my first new Harley. As for your gear-change problem my 1990 bike, bought new, broke its gear-lever return spring. When we change gear, that spring returns the lever to the natural position, from which we can make the next gear change. It resets the internal positive stop mechanism, in the gear selector.
If my diagnosis is correct, you should find you can change gear (I rode mine a lot like this) by using your toe to return the lever to its proper place. The long-term solution is to replace that spring, which costs a few dollars, but requires a lot of effort to get to. I had mine done, but IIRC it involves removing the primary drive, so you can remove the gear cluster from the trans casing, to get at the darned spring!
Been there fixed it. Just as Graham post 11 described.
Had the same issue with my '89 last fall. As Graham described it is shiftable as is, but definitely a PIA. Also as Graham mentioned, the spring itself is easy and cheap to come by (it will be in stock just about anywhere - my local indy had one, didn't even have to go to the dealer), but replacing it requires a fair amount of disassembly.
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