Hello thanks for the welcome!
My property isn't so big but steepness and other terrain concern me with a basic craftsman riding mower. The other consideration is value and amount of use it will get compared to cost.
I've been mowing about .4 acre of steep lawn with a Honda walk-behind 21". It takes forever and is a lot of work! I can use the exercise but 3-hours and 2 tanks of gas is too much wasted time.
I suppose some would say get a wide-area walk-behind. Cut my time in half, maybe, and still have good tight space/trimming ability. Could maybe even sell off the Honda and just have one machine.
On the other hand, I'd like to have a mini-tractor, like a Kubota BX or John Deere X739 or something. I'd make up projects to play with that!

:dance1:
I test drove both the Toro and Cub Cadet ZTR-steering wheel machines. I liked the cub better, seemed smoother operating. For $3000 though I wonder if they are versatile enough. Also wonder if they will hold up on the slope pulling a cart.
I test drove a Husqvarna 322T "Swedish Rider", also. Unique machine. I like a lot about it, the front deck gives good visibility, ease of maintenance and attachments, the AWD would be nice on the hill and in winter if I get a snow blower, the tight steering will make trimming easer, less to do with a push mower or string trimmer. Drawbacks are its high price $5000. Not a popular design in USA.
Also, had a dealer bring out a used john deere x485 with AWS 54" deck. It handled the slope without any trouble. Except when damp, did have to use the diff lock a couple times. AWS was kind of funky to get used to. Cut some tall thick grass easily. Didn't leave a great finish. I think it had 500 hours. They wanted $6500 and it didn't seem to be that great of condition.