Walking on footpaths is fine, no worries. We would do a 30 minute walk each night on footpaths (fairly poor condition ones) each night with DS1. Across grass, rocks etc it is fine for short distance or lower speeds. Even taken it on sand for beach trips. Firm dirt footpaths are fine too for longer walks - some might say it would be a bit bumpy for the child but we've never had any complaints.

We didn't get the cocoon as DS1 was a Sept baby in sunny Qld. We had him in it from a newbie.

We don't have a skate board, but we are considering getting one so DS2 (2yo) can ride while DD (6 months) is in the pram. I think the board would be fine, particularly if you had the handle extended tall, so they stood inside the handle.

The newer bee has connectors for a capsule (which I would have loved!), a more streamlined look and the seat goes bolt upright for an older child, where the older one still has a slight recline.
oh fantastic, thanks so much thats really helped!