Tim,
I still REALLY think you should consider the 3320. It is not so big as to be not manuverable but is big enough to do any task you wish. Yes, it is more expensive, but it is also more tractor. Flat platform, tilt wheel, much stouter hydraulics, LoadMatch (worth its weight in gold on this machine) are just a few of the features that make it worth checking out. It is not a lot larger dimension wise to the 2520 but weighes a lot more, which means loader work and ground engagement tasks go a lot better. Despite this, my 3000 series mid frame I owned would mow as well as my father's 335 in finish cutting, would do it a lot faster and use about half the fuel, even though it weighes five times or so more!!! Seriously, I do not think you could make a mistake with any of the machines, but from my past experience, please do not buy too small. I have in the past spent more money upgrading from a "too small" machine to a "just right" machine than I would have just going with more to start. You might find that you fit on a 2305 or 2520 just right and one of them is exactly your cup of tea, but for me, about five minutes after riding a 4115 and then hopping on a mid frame sealed it, especially when I saw how little the difference in price was for the larger machine. You can also haul it well on a 16' tandem trailer, which is really about what you would need anyway for a 2520, based on its length. Weight wise, they could both be towed with a half ton truck if you will be needing to transport them much.
John M