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Re: 2nd gear problems
Your teeth are worn on second gear. You'll have to disassemble the transmission to fix it. Sorry for the bad news. If you have a shop manual, Clymers or Haynes manual the procedure is quite detailed. Not something I would do myself unless you have a lot of experience.
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Sounds like a bent shift fork. While accelerating you can feel the power cutting in and out quickly. The problem will get worse if you keep pushing 2nd gear till it slips. You can learn where (at what RPM) it wants to jump out and start shifting before it jumps out. The long term fix is opening the transmission and fixing the bent shift fork.
The transmission "neutral" position is located between 2nd and 1st gear. You say you're also getting a "false neutral" between 3rd and 2nd. Since you say you're finding both, it leads me to suspect that you are not being aggressive enough when shifting the gears. The Sportster has the best shifting transmission of all the Harley motorcycles. Since it does shift so easily, riders sometimes "soft shift" the transmission and wind up missing gearshifts. This is the most likely problem, rider error.
Now, there is the possibility that the clutch is dragging but that usually effects the transmission when upshifting, not so much downshifting. With the engine off and switch on, put the transmission in gear, hold the clutch lever in, press the starter button. If the bike tries to move forward, you need to adjust the clutch.
More likely it is a slightly bent shift fork not fully engaging into second. The clutch and bearings are not suspect. Remove your foot from the shift lever then go full throttle in 2nd. Those new riding boots may be doing the magic unconsciously. Adjust the shift lever height if that is the problem.
You have a bent shift fork. This is not a repair job for the amateur. The engine comes out of the frame, turns upside down then the bottom of the gear case gets separated from the top. The entire shift drum, forks and all, gets removed and the bent fork gets replaced. The engine re-assembles in the reverse pattern.
Now what about stressed gears? Any cracked or broken slider gear dogs?
You are going to have at least 75 parts on the work bench. Was the collar on the slider gear on the left side or the right? I am trying to show you why you had best be careful. The shop charges more to fix a box of loose parts than if they fix a gearbox.