Well I put a lot of hours in both, and I'd give the edge to a late-model 1086.  Quiet enough to not ring your ears, and they are actually easier to wrench on for the most part.  AC components are better and easier to access, changing a starter is a breeze compared to a 66 with cab.  You will always get a lot of derogatory comments on here about a 1086 cab, but they come largely from people who are now used to Magnums, Challengers, 8000 JDs, etc.  Have to remember the perspective that a lot of people who bought new 1086s, or 66s for that matter, started out farming with horses or steel wheeled gas tractors-and for them just having a cab to get out of the elements was a quantum leap.

All that said- for the minimal price difference, I'd sure consider a 5088 or 5288.