TfL are not as to blame as you seem to make out. Fares beyond West Drayton are set by GWR. This March it is the fares within zones 1-6 which will rise as the NR (GWR) set fares are all frozen. If GWR/SWR asked for an OSI at Windsor and priced fares accordingly then TfL would set it up. Travelcards with validity in zone 6 are available to use on the Elizabeth line trains to Heathrow. That is how people making a return journey aren’t penalised with the fare grab being aimed at tourists making a single journey.
Now that the new revenue contract has been settled I am hopeful that we’ll finally get some movement on discounts with contactless. As I understand it, the main sticking point is NR needing to know that a railcard is attached so they can ask to see it. Adding an extra list to the inspection devices makes it not an off-the-shelf blacklist/whitelist application, and clearly nothing can be written to the bank card.
I’ll not offer any defence on delay repay, other than it will have been agreed with the DfT when signing the contracts.