Been there done that, owned the 585 and now a 2210, and they are two different animals. If you are just wanting to cut grass, plow snow and no desire for tractor functions, then the 585 wins hands down. As a suggestion, I would go to one of the large auctions and get one there. If you can't find the locations, then email me on the side, but I watched nearly 15-X585's sell last Friday for around $7000. If you get one at 7K, you will not get hurt down the road on a possible trade, but buying retail/new on these you will get killed on the backside. I also did a cross search in MA and there are a number of them close to you between 7-8K and I bet they will bargin at this time with the new X700 series about to step out, plus there is a $500 rebate on existing ones, so the used must be suppressed even more. Alternatively, I just saw a 2210, 210 loaded and 62" mower deck in the paper for $9800 and 70 hours.
The point I trying to make is you can get a good used machine with warranty and be carefull not to miss purchase up front, because like myself and many on this site, it simply cost more $$ to correct the mistake down the road by wanting to "up grade".