Stormchaser,
The difference between those two mowers is that the 1060 is an "economy" line mower. The economy mowers and the 2000 series are both currently manufactured for John Deere by Woods. The main differences are as follows: the 1000 series has a lighter gauge deck, all are rear discharge, they have a slightly less beefy gearbox and pulley hardware, and a slower blade tip speed, so they would not cut quite as well as the 2000 series in deep grass or at higher ground speeds. There is absolutely nothing wrong with the 1000 series decks and they are somewhat cheaper, but if you have the cash, spring for the 2000 series. It is much heavier duty and cuts fantastic. I have a 60" side discharge for my tractor, and the results are amazing for such a big mower and a large tractor. My 2060SD cuts better than my father's 335 garden tractor!!! I do not like the rear d/c mowers because if the grass is wet they blow clumps out the back. They also do not "stripe" quite as well. I have not missed not being able to trim on one side. I have regretted that I did not get the six foot for my tractor. I changed my mind at the last minute because of concerns about mower overhang when hauling. This was a mistake.
John M