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I can't recommend a tedder without knowing where you are located. If you're in the midwest or east then I'd definitely recommend a tedder, especially if you aren't using a conditioning mower.

I considered a drum mower when I was first getting into it, my biggest drawback was they didn't condition the hay and were narrow widths unless you had a huge tractor. If a field is bumpy it limits you from going too fast anyway, so then you just spend more time in the field due to less machine width.

I think a good machine for him would be a 9' haybine. I'd recommend something like a New Holland 488. They can be found all over and New Holland still makes them brand new to this day. They've been making them since the late 70's or early 80's. You can find them for around $3-3.5k+. They're considered the gold standard for haybines. Nicer machines will cost more of course. If you go the route of a haybine, be sure to inspect the rubber conditioning rolls to make sure they aren't peeling rubber excessively as the rolls are very expensive to replace, or you can keep them but won't have conditioning capability. In checking out a mower you'll also want to look over the wobble box to make sure it doesn't have any excessive play. One thing to do is try to cycle the machine by hand by the wobble box belt.

If you can move the wobble box belt to make the sickle bar move then that indicates the sickle is in good adjustment. If you cannot move it, that suggests there is binding on the sickle (it is poorly adjusted) and could spell problems for the wobble box.

On my 488 I can pull on the wobble box belt with very little effort to cycle the sickle with one hand.

He'll want 4-5 hay wagons with nice running gears (Deere gears are good), or lots of trailers. Even in a 5 acre field in first cutting, you can fill up 4 wagons real fast.
 
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