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Was given a BARELY used John Deere L100 lawn tractor originally purchased in 2013 brand new. So after a jump start, it started right up, slightly rough idle. Let it run for a few, mowed a few rows. All good, shut it off. Afterwards would not restart so I started some maintenance items. It has been able to start several other times over the past week. Seems random on when it will and won't start.

1. Changed spark plug, set gap to .030"
2. Fuel tank was empty, changed fuel filter (whew stinky)
3. Filled tank with fresh ethanol free fuel
4. Checked oil, in very good condition. I plan to change oil once the starting issues are resolved.
5. Checked air filter, virtually brand new
6. Bought and installed new battery. (Started nicely right after that)

Why is it so random in when it does and doesn't start. Where should I go next?

If the unit was stored for that long with any fuel in it, and I suspect it was, you are going to have to remove,, clean and rebuild the carb. I’ll bet the inside of the carb will look like crap and you may even have to replace the carb.