Why is that overpriced? What other 27 HP diesel tractor with mid-mount mower and FEL can you for $14,000?...
You can get a JD X748 comparably equipped for that price. It will have a 24 hp Yanmar diesel which I would take any day over the 27 hp Kohler.
You would also get full-time all-wheel-drive instead of on-demad 4WD.
So here's the bottom line, it sounds like--the Legacy XL is a good tractor that is probably most comparable to the BX2660, Bobcat CT122, or John Deere 2305. None of these tractors are an exact match, though--for instance, the Legacy XL has the best cut and the most HP out of these tractors, but it also has the lowest FEL lift capacity and weighs the least (which could lead to traction issues if you're pulling a grader or pushing snow--but it also means you are less likely to put ruts in your lawn).
Is that a good summary?
I would disagree. I don't think the Simplicity XL, a GT, is in the same league as a Kubota BX2660, JD 2305, Bobcat CT122 -- all of which are SCUTs. Except for the hp advantage, I don't think it's even in the same league as the Kubota BX1860.
I could be wrong, but when I compared these a while back, I gathered that in order to operate the FEL, the Simplicity needs to have the sub-frame re-inforced. By comparison, the JD X700-series does not need sub-frame re-inforcement to operate the FEL (the frame is built more heavy-duty).
Don't get me wrong, there is definitely a market for highly capable GTs. For some people, they make more sense than a SCUT. So it's not just a question of cost-comparison. You need to make sure to find a tractor that fits your needs. It may turn out that a smaller tractor that fits your needs ideally could cost you more than a larger tractor that doesn't.
But if the Simplicity is the right size for your needs, you should definitely be comparing it to the JD X700 series. The X700s are a better comparison than the SCUTs.