John makes a good point. It's one I'm wrestling with. I've got some open pasture, around 15 acres or so, of nice flat level hay ground. Just mowing right now, but the field needs a good discing and some seeding, and subsequently some baling. It's not a business for me, just a hobby, but a utility tractor suits my needs perfectly.
However...
On the north side of the field is the creek -- full time, year round, big old concrete bridge and such. The creek has created a very nice rolling "park" area underneath the shade of many sycamore and cottonwood trees at the base of two very decent hills. I'd guesstimate I'm looking at another 5-10 acres of maintenance in that area. I had a NH TN75S in there last fall, and I just couldn't manuever amongst all the trees, gullies and washouts. The direct, geared transmission endured tons of clutching and shifting to navigate or accomodate all the varying terrain. My current TC29D with hydrostat was quite adept here -- small but nimble.
Then...
We have the two hills, about 25-35 acres combined. I've cut trails from the base gully to either side, and they are heavily wooded with oak, cedar and one very populated pine top. Space requirements here are very tight, but big enough for the TC29D and the next size up "compact" tractor. No room for a "utility," though. And, in the next few years, we'll be cutting a road and building a house near the aforementioned pines, which will net me about 1/4 to 1/2 mile of driveway.
To say the least, I need a "swiss army tractor." Something big enough to keep the field mowed, occasionally run a smallish disc slowly, drag around a small square baler, maneuver and mow down by the creek, fit on the hills for general cleanup and run a future snow-blower for the driveway. To top it all off, I've had allergies all my life that seem to be getting worse as I've gotten older. So, my wife (!!!) is insisting I get a cab so I'm not so miserable after a day of tractor work. That makes for mightly slim tractor pickings.
My search has mostly narrowed to the Kubota Grand L30 series. The cab is quite nice, and the 5030 sports some decent HP to do alot of different chores. The mid-PTO is appealing. And while the HST might be marginal for the light discing, it's perfect for everything else.
Nevertheless, I'm still fighting with doubts as I try to optimize the purchase for my environs. Sometimes, this can be difficult, and I sympathize with the original poster if he faces a similar dilemma. However, this is a good forum, and I think if we knew a bit more about your property, we all might be able to offer more directed wisdom.
Later,
Jay