2. The 08.56 'off peak to Reading and beyond'. If it can be off-peak for those stations (and which are they? Does 'beyond' mean Paddington?) why cannot it be off-peak to get to Swindon or Didcot? I know what the answer to that is - that it arrives at those before 09.30 - but I doubt that the numbers wishing to get to Didcot and Reading using this service justify what appears to be an artificial discrimination against them, which is how it feels to a potential passenger.
Now I don't see it that way at all.
As you say the rule (seen as much in the breach as the observance) is that off peak tickets are valid after 0930. It will of course depend on the actual restriction code for each journey, but most passengers won't know about that (even I didn't until an argument at Paddington some years ago about whether my off peak return
CPM» to Hitchin was valid for return in the evening peak
)
The wording says "off peak to Reading and beyond" and that is exactly what it should say. Whilst it is true that the train in question only stops at Paddington after Reading, there may be passengers changing at Reading to go somewhere else (eg Henley, Maidenhead, Slough, Windsor, Guildford - its a long list) who are also permited to use that train.
As regards Peak versus Anytime, I wouldn't like to draw a conclusion one way or the other. I've never liked "Anytime," preferring the good old fashioned "ordinary return." It is possible that some passengers don't know what anytime means whilst alll they have to do is look at their ticket, and if it says "off peak" on it they ought to be able to fathom they can't use that train.
I suppose to cater for the less railway-savvy it is best to use the term "peak" rather than anytime, because there is always the chance that some 'erbert might think his season ticket or all line rail rover isn't valid because it doesn't say anytime on it...