Once a battery is drained down enough to make cranking over your engine fast enough to start the tractor impossible, just jump starting will not work. You need to either replace the battery, or have it load tested, AFTER it has been charged by a regular charger long enough to bring it up to full, or as close to full charge as possible. Then, when it has an induced load placed on it, it will either pass or fail the test. Fail indicates new battery time. Pass means you can reinstall it and get whatever life is left out of it.
Batteries need to be kept at 80% charge and up. Once one lets a battery sit, without using the machine it is installed in for long periods of no use the cells start to sulfate. a TRICKLE CHARGE IS NOT ENOUGH TO DESTROY THE SULFATION, HANCE YOUR NO START CONDITION. (Sorry, caps mishap).
A battery tender, or using a battery isolation switch to 'disconnect' the battery from the tractor without removing it, could keep the same situation from repeating.
However I suspect you will need a new battery since you've been killing yours for some time now.
And while it's out, before installing one, same or new, clean up the ground at the frame and both post connectors until they are all shiny metal. Then coat the chassis/frame ground with battery protector spray, and do the same at the posts. I also use the anti-corrosion felt washers to help reduce oxidation/corrosion.
If you still have starting issues it's time to cut back the plastic insulation jacket at the frame ground of the negative cable, and see if there is presence of corrosion under the jacket. Is so, or presence of same on the positive cable, less common but not totally unusual, then replace either cable showing corrosion. With the positive cable make sure the battery is disconnected at the ground post (negative side) of the battery before cutting back the jacket.
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