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Nelle - he didnt like his head being covered (i.e the fabric being against his head), and he wasnt able to hold it up so there wasnt a choice.
I had him upright in it with the fabric pulled across.
He was a summer baby though. this one will be autumn/winter so it may be less of a problem
Rainforest - I would definitely go with the double Mountain Buggy over a P&T if you're going "off road". I have a double Valco for going on proper walks and a P&T for shopping. I find the P&T is nowhere near as stable as the double - no problem on nice level floors in the shopping centre but the couple of times I've used it for walks simple things like easing it up and down kerbs I find there is a huge difference in how confident I feel that it wouldn't tip. I would have bought the double MB (I had a single MB before DD#2 came along) but couldn't justify the money for that and a P&T - knew I needed something smaller and lighter for getting in and out of the car. HTH
Rayray - I agree with the others and would be going for a skateboard attachment and a sling. DD#1 at 17 months would much rather walk than be in the pram (I'm just happier with her tied down!!) so I can imagine that a 3.5 year old would absolutely be happier walking. I used the P&Ts for both of them as well as sometimes having DD#2 in an ergo initially, then when DD#2 was about 2.5 months until recently I was happier with her in the ergo - she wasn't big enough to go into the toddler seat but was too big to look comfortable in the newborn position in the pram anymore (and she's a little girl, although quite long). Might have just been me, but it just didn't look big enough.