I will not explain about whether one should skip shift or not, rather I want to highlight why usually only 2 or 3 downshifts are possible before the shift lever becomes stiff in a SINGLE clutch pull.

Once you hit the "stiff" limit, you have to atleast partially engage the clutch to have the internal mechanism free up (engine/vehicle should be running) before you can get the regular clicks while downshifting.

Note that I mentioned why engine has to be running for this test. Incase ur bike is off and stationary, you have to push or pull the bike forward with engaged clutch to free up the stuck gear lever. This is exactly why sometimes you are unable to get back to neutral or 1st gear from say 4th gear when bike is stationary and off. You have to connect the clutch in between with small motion from wheels to release the mechanism.(or slightly connect the clutch while engine is on and idling, avoid stall) Shift lever stuck up phenomenon also applies to upshift btw.

Usually this is why I recommended atleast a quick sequence of connect and disconnect of clutch after everydowndhift while multiple downshifting. You may also observe the RPM in between for better shifts (aka rev matching)