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I like my 4035 and it would do what you want. The "new" version of the 4035 is the 3540. The 1538 would also be an awesome choice out of their new lineup. Both fit the budget and the acreage, but both can easily exceed the $25k mark depending on what all is added to the base units.
Beyond that though, I really feel the need to ask; No neighbors do hay? Perhaps a neighbor would hay it for free, for free hay. Hayfields this far south are just getting their first cuts, I'd imagine up there they'll starting anytime in the next couple weeks. If it is good pasture grass, it might be a better solution than destroying it with a rotary cutter (they don't do great on grass).
If you plan on cutting it with a bushhog/rotary cutter, it is best to do it once the grass has went to seed. It allows it to reseed to replace what gets killed off by the cutter.
Running a bushhog regularly over pasture grass in an attempt to make it look like a lawn results in a lot of weeds. The blades on a rotary cutter are very thick and use a rather blunt angle on the cutting edge so they will shatter small bushes, sticks, and limbs. They more or less tear and shred the grass rather than actually cutting it. This will kill the grass. If it isn't getting tall enough to reseed itself, you must seed it or you will end up with a pasture of dandelions.
If you plan on cutting it more than 2 or 3 times per year, get a 3 point finish mower.
