I'd definitely look into what dealers you have and their reputation. We had a 33 hp MT 265 challenger, supported by agco, it saw quite a bit of use, and I have serviced and repaired it prior to its later years at the farm. I never ran into any obstacles, it gave quite a few hours and use, but was outclassed, we needed something much larger and they have a NH there now, forget the model.
The challenger was hydrostatic, you'll want weather protection from a blower, handy and easy to operate, they are narrow and not as stable as a similar size utility tractor of the past.
Dealer/parts support and re-sale comes to mind with any of these, so aside from brand and specifications, it would be good to know what you have there first. With so many out there today, I'd have a fun time even considering which direction I would go in, hopefully you'll do better LOL!
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