The pickup on a 14T does not turn as fast as the later bailers. The 3.5mph speeds sounds about as fast as that pickup can handle (3rd gear on a 3020). 2.5 mph was a common bailing speed for our 14T (2nd gear). Your tractor's low range sounds ideal for baling.
With flat fields and only mild hills your tractor should be fine pulling the bailer and wagon. If you push it, a 14T bailer will take in enough hay to pull down a 34 HP tractor engine. I'd be more concerned about the tractor's engine overheating than the transmission. Watch the gauges and slow down if the tractor gets too warm.
My only concern would be at transport speeds. Slow down if you try to pull a full wagon behind the bailer at road speeds. The total weight could push the tractor and get squirrelly if you need to stop in a hurry.
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