I never realized easy the Sportster was to work on until I got a Dyna, LOL. My kickstand doesn't snap up like it should. Feels like it's lubricated with Play Dough or something. A quick look under there with a flashlight showed lots of gunk around the bolts. My dilemma is my limited equipment. The (modded Harbor Freight) bike jack I have will only sit under the bike at one particular position. Once in the air, the kickstand hits the jack, so I can't put it up all the way. The issue is the spring, which has too much tension when only half up.

After mulling this around in my head for a day, I tried something else. Here's my steps for anyone interested...

1. Make sure the transmission is in first gear so the bike won't roll.
2. I put the jack as far forward as I could. When raising it, one of the jack rails lifted the bike at the front of the frame, the other rail was up by the front tire, not touching anything. I raised the front up enough to be able to retract the kickstand all the way while keeping the bike stable. Rear wheel was still on the ground. It worked pretty well.
3. Remove the spring.
4. CAREFULLY lower the bike on to the kickstand, which now has no jiffy spring, so obviously make sure the kickstand locks correctly into position, or it's going down!
5. Position the jack to normal position and raise the entire bike nice and high.
6. Remove the pretzel clip and bolt and pull the kickstand assembly out. A long thin flatblade coming in from the side helps with the pretzel clip, btw. Ditto for reinstallation.
7. Disassemble, clean all the parts with brake cleaner. I removed lots of old grease, dirt, and some Play Dough.
8. Reassemble using antiseize lubricant.
9. When reinstalling the bolt, use blue threadlock.
10. Reinstall the assembly, slide in the bolt and attach the pretzel clip.
11. Now CAREFULLY lower the bike on to the jiffy stand, again, being sure it's in the right position so it locks into place when the bike is leaning on it.
12. Move the jack back to the front, raise the front so the jiffy stand can swing freely. Note - if you go too high, the jack will tilt, so watch that.
13. Reattach the spring.

Once all back together, the stand moves up and down a lot better. My spring is 4 years old, a new spring would probably make it snap back a little faster, but the stand stays put against the bumper so it's OK for now. It can be replaced without going through all the above, so I'll probably do that sometime next year when I'm bored.

Before...

 

once a year I put mine in fist gear and lean it way over with the throttle against a big oak tree... then I do the remove/clean/antiseize/re-install.

flips out like a switchblade...

 

i just had to change my jiffy stand spring this weekend. While i dont have my motorcycle jack here at my worksite, i used an old dirt bike trick from my dirt days

It was sketchy at first but then i realized it was actually quite stable

A strong tie down strap to the hook in the bed of my truck then i crawled underneath and replaced the spring...