I've got 5 acres of pasture, never let it grow out so I'm taking off at most 4-6" at a cutting. Will my B2710 pull a 60" bush hog through that? It's flat as a pancake here and the ground is reasonably smooth.
If 4-6" of grassy growth and the machine makes 27 HP then as long as the tractor can pick it up it will cut the feld no problem.
I'll add that just because the hog is 60" wide doesn't mean you need to take 60" wide cuts. You can overlap three feet to make it a 2 foot cut. The first lap will be slower since it will be a full 60" cut.
As long as your machine can be hooked to the cutter you can get it done.
I believe our new B7610 is a few hp smaller than your B2710. I went with a KK 60" with some hesitation, and the few hours I put on it last week went well. A little difficult going up terraces, but no problem in heavy grass on flat areas.
Every year I help my buddy cut 5 acres of chest high weeds. He calls it pasture when there are horses around to keep it under control. There haven't been horses there for a while.
The 5' BushHog Squealer I use is powered by a 24hp JD 855. It has 19 hp at the PTO. The tractor is working a little bit to cut that tall grass and weeds, but I wouldn't choose to go with a smaller cutter. I don't think your 27hp will have any trouble.