You don't have to worry about the resale value of the 250. That goes for both the 2000 and 2008 models. Personally, I think that's a great deal for the 2008, and that 4-yr warranty is a big plus.
However, if you are just learning how to ride a bike, it is very possible that you will drop it at some point, and it might be harder to swallow a drop on the 2008 than the 2000, but that's different for every person.
The price for the 2000 is a good one too, but what I would worry about is that it only has 8500 miles after 9 years, as bikes just sitting can deteriorate fast; but if you know for certain it has been well taken care of, I wouldn't worry about it.