My bike is still new but I have noticed that the bike seems to start on its own terms. Sometimes it fires up with kickstand down, sometimes I need to press the clutch, sometimes I need kickstand up AND clutch pressed in, etc. And I always park the bike in neutral, I never shut it off in gear (because I may forget it's in gear when I go to startup the bike).
I have noticed the best shot is to just press the clutch in, regardless of neutral or kickstand position. You should not have to crank the bike 30 times or so just to get it to turn over. In your case, I would twist the key, put the bike in neutral, bring the stand up, press the clutch, and start.
You don't want to run down the battery and risk being stranded and you don't want to run the starter motor too much; manual says no more than 5 seconds of cranking I believe or it will over-heat.
Last edited by MrElusive; 08-30-2019 at 02:56 PM.