Whenever I've lived in a place with a yard to mow, I always thought the thought of having to do it was worse than actually doing it. That said it was never in a place with difficult yards
I had a tiny push mower to cut my grass when I had a 20' by 20' yard, then I bought my house now, that has 1.5 acres and cut it the first 3 months with that same push mower. It took me almost 3 days just to cut, working on it after work. I was miserable because in the summer down here it rains every day and the grass has to be cut about every 10 days.
Some of them return to charge on their own, so it doesn't really matter as long as they are getting it all cut regularly.
Sure is, cost me $80-90 for about one acre five to six years ago. Of course it is not an easy yard to mow.
When I moved in, had an aged small Lawn Boy, took me two days to mow. Bought a Diesel powered Kubota Tractor with 3 speed trans, found it still took several hours with much mowing requiring a push mower and/or weed eating. I've gone full circle, went from the Kubota to a self-propelled, and now am using just a push mower, takes four days, but I use it for exercise and therapy. Still have the self-propelled.
It was a nice little garden tractor, but my yard is just too uneven and steep. I turned it over once, and came close about once per mowing. I sold it to my Uncle who already had one just like it.