It must depend on WHERE you are. It takes 350 hp 4wd or so to pull a 44' in NE IL. With a 2wd tractor, traction can be "iffy" sometimes, depending on the surface  you're running on. If you're working on fall chisel (or now moldboard), you'll take a pounding sometimes w/2wd tractors. It's amazing the difference just going to a MFWD.

But anyway, I'd say if the original question was in NE IL, they would be happy w/25-27'. Not saying he couldn't pull slightly bigger, but you might have to drive stakes to detect movement.

Good luck.

1st photo is about 1953-54? MM UBD on maybe a 10' JD fc w/a 3 section rotary hoe behind it. You didn't back up very far.

2nd photo might be closer to your question. IH 27' fc on a 4760 2wd. Obviously from 1992.