Yes, railcard with me at all times (even in Beirut!)

My routes (for now, maybe more later) are (all return):
Paddington - Slough - Windsor
Victoria - Hackbridge
Paddington - Bath
Vauxhall - Hampton Court
Waterloo - Salisbury

If they are gates, do I have to 'touch in and touch out' (well, enter ticket) or only in?

Next question: when they say 'any permitted route', what exactly does that mean? Any combination of trains? A direct train? What about when they say 'off-peak' - how will I know which one is peak and offpeak?

Thanks!