Bret - I agree, go one piece at a time. There's a LOT to be said for new - reliable equipment. But I'd keep your old stuff as backup. You always need backup, no matter how good your equipment may be.
First, I'd take a serious look at drum mowers.
Relatively inexpensive, even brand new, and from what I read, fairly reliable, cheap to repair, and work pretty well.
I'm still on the fence about them myself because I'm not sure about not having a conditioner like a disc/hay bine. But I've talked to some people in this area that love them... So, I can't say you should buy one, but at least research it as I am.
To replace a 7' haybine with one shouldn't cost you TOO much - and you should then be able to cut faster, and very reliably.
Would love to hear other's opinions on them here.
If you can't cut, you're dead. And if you can't bale you're dead. Simple as that.
So after getting a good cutter - I'd look at improving the baler situation.
Of couse raking and tedding IS very important as well - but... if completely DESPERATE you can at least sort of ted with a rake, and you could theoretically bale without raking if you absolutely had to. So I'd put those purchases off till later.
That's assuming all equipment is equally near death. Obviously if one item is causing the most trouble, replace that first.
And - assuming you've got a good reliable tractor.
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Today's Featured Article - An Old-Time Tractor Demonstration - by Kim Pratt. Sam was born in rural Kansas in 1926. His dad was a hard-working farmer and the children worked hard everyday to help ends meet. In the rural area he grew up in, the highlight of the week was Saturday when many people took a break from their work to go to town. It was on one such Saturday in the early 1940's when Sam was 16 years old that he ended up in Dennison, Kansas to watch a demonstration of a new tractor being put on by a local dealer. It was an Allis-Chalmers tractor dealership,
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