I have mobility problems and the reason I was recommended an Xplory was because they are easy to push.
I try to stay on firm ground as I don't walk very well, so didn't have much experience of other terrain (apart from sand and snow which it didn't like much - but then neither did I!).
I kept the pushchair facing me with both DC so that I could hear what they were saying. When they were old enough, they just walked. DS1 used it until he was just over 2 when DS2 was born and DS2 last used it when he was almost 2 1/2.
Apart from when we were out and no highchairs were available, I didn't turn the seat round. It could be lowered when necessary, but even with my bad back I didn't find it too much of a bother to pick them up at that age - I found it far harder getting them into the shopping trolley at the supermarket.
It might look a bit odd, but I had very few negative comments - most of the time people thought it was a great design when they saw that I could talk and interact with the boys and I could put huge amounts of shopping in the bag at the front.
I could lean on it heavily when walking and it never once even remotely looked or felt like it was going to tip over.
I can also recommend the changing unit which was safe and big enough for the boys even at 2 when I had to do nappies (getting down on the floor and particularly up again was hard). It is a large piece of kit, but was worth it for me. However, we will not keep it to turn it into a desk.