I didn't get the rears on my 2150 filled when I bought it 12 years ago, out of ignorance, and because the dealer didn't suggest it. Regreted it many times when doing FEL work on slopes.
I had the tires on my new 7800 filled, and am quite pleased with the results. One place where I most notice the difference is when using the box scraper rippers in the woods, when they often get hung up on roots. Without filled tires, the lighter tractor can just sit there and spin the wheels. With filled tires, the extra traction allows the tractor to dig in an rip right through the same roots.
The tractor is also a lot more stable when going up/down or across slopes, which is a very real benefit.
The dealer didn't charge me for filling the tires.