It would depend on how long you are going to keep the tractor. The IH 5288 is a pretty good tractor but it was only made a few years. There are few after market parts available for it and who knows how long CIH/Fiat is going to keep the part available for it.
The JD 4640 is a good tractor too. They where super reliable unless they where turned up sky high. I have seen them running 225 hp. Then the main clutch would get dicey. The biggest advantage is that the JD 4640 shares a lot of parts with the 30 and 50 series. There where many more of them made. So there are a lot of after market parts available too.
I would lean toward the JD 4640 if you do not need 540 PTO. IF you need/want 540 PTO then go with the IH 5088.
The JD will ride way better than the IH 5088. The 86 and 88 series where like running a bucking bronco in rough ground.
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