Welcome. Because of your admitted lack of mechanical experience I would start transitioning to what ever color equip. dealer is nearest you. That may or may not be JD. If you want to stay with the JD line then I would surely get a 4440 in the mix. I think I would consider trading the 4520, 2940 and 2840 for a low hour 4440. Warning! Nice low hour 4440 will command a premium price but they are worth it. That would pull the 18 ft. disk/basket real nice. If your nearest dealer is red then perhaps a 1086.
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