you won't get the kill you'd like to have if you wait until after frost to spray Roundup. I'd also question the quality of your hay if baled at that point also.
My suggestion is that you probably should get the hay off now, let the pasture green back up some if you get the rain, and spray around Sept 1. Having a custom applicator for that acreage is probably best, they shouldn't be too busy that time of year. Probably looking at around $10/A for application (top end) and $7/A for chemicial (top end)
If you do it yourself, you'll need a pump, boom, nozzles, then calibrate it to know how to mix, and what speed to drive. Quite a bit more to spraying than just dumping it into a tank and slopping it out on the ground. Alot of folks typically run 10-15 gallons of water/A, and run 1qt of a generic glyphosate/acre, though for killing fescue, I'd suggest a stronger rate, more like the 40-48oz/A rate like you've been told. Also need to mix in a product called AMS, it's a spray grade Ammonium Sulfate that helps soften the water, inrease absorption, and tie up cations that can otherwise tie up the glyphosate molecules.
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