Welcome to the forum Chris. I have used a machine similar to the AS for a number of years now, so maybe my limited experience may help. I spent many hours looking for a grass eating machine to be used in much the same way as you describe. My wife does the lawn cutting and she wanted to go from a walk-behind to something she could ride on, while I wanted something that could handle the steeper slopes in the fields. A ride on "brush cutter" was the obvious choice and after trying one out, I was pleasantly surprised to find it would still give a decent enough cut for a lawn.
When you look at different models, one thing to consider is how high the deck can be raised. On some models I looked at the highest position available was not much more than a couple of inches off the ground, which for me was not enough.
Some manufacturers offer different cutting widths. Bigger decks usually come with wider wheel spacing, making them more stable on uneven slopes. Spec data assumes perfectly smooth slopes, but in practice there are always ridges and hollows and the narrower the machine, the more significant that becomes. Double wheels would help but as you said they reduce mobility. Another consideration with them is that you can't cut as close to fence lines etc.
For stability specification, I believe the standards on European machines calls for the quoted side slope angle to be half of the measured tipping point (someone please correct me if that is no longer the case), so a reputable machine that claims 20 degrees should actually not tip over until it gets to 40. Sitting on a machine that is cutting a side slope at 20 degrees is not that pleasant an experience unless you have a fancy gravity compensating seat, whereas if you take that same slope closer to straight up or down and then only turn side on with care, ideally where it is flatter or if not, slowly and where you can see there are no bumps or hollows, you will enjoy all your slope cutting. If you get a 4 wheel drive machine, you can easily go up and down on the steepest sections without turning at all, although driving in reverse for long periods may give you a stiff neck too !
The AS looked to be well built and I think it used galvanised steel, so should last a lifetime. I wasn't able to get a demo from anyone locally on one of them, although it now looks as though more dealers sell them. This is what we have.
One other thing about all these machines - they are way more fun to drive than a normal ride on mower
