The TRO is The Waltham Forest (Prescribed Routes) (Winns Avenue Pennant Terrace region) (No.1) Experimental Traffic Order 2023 (https://drive.google.com/file/d/1GUvqn8W6Fhz-HNdysI7JQFRvPcJKQk6u/view).
Sorry to say it but the signs look clear as day, even at night:
https://www.youtube.com/watch?v=kF6RUisguFg
The case you've cited is negated by paragraph 5 of Schedule 1 to the London Local Authorities and Transport for London Act 2003 (https://www.legislation.gov.uk/ukla/2003/3/schedule/1/paragraph/5/enacted), which provides that:
5(1) Where a penalty charge notice is served on any person and the penalty charge to which it relates is not paid before the end of the relevant period, the enforcing authority may serve on that person a statement (in this paragraph referred to as a “charge certificate”) to the effect that the penalty charge in question is increased by 50 per cent.
(2) The relevant period, in relation to a penalty charge notice is the period of 28 days beginning—(a)where no representations are made under paragraph 1 above, with the date on which the penalty charge notice is served;
Maybe Hippocrates can come up with something else?
One argument I can see is that the traffic order says:
2.7 No person shall cause or permit any motor vehicle to enter or proceed in Winns Avenue, E17, between the eastern kerb line of South Countess Road eastwards for 16.5 metres.
However the signs are not placed at that distance:
(https://i.imgur.com/BnFo2FC.png)
This has won for instance in Michael Dempsey v London Borough of Enfield (2230348292, 26 August 2023) (https://drive.google.com/file/d/1gm5wYAaOUAoy98tzestBeUbQZq4M-dka/view), as Mr Teper accepted the regulations require that "When the sign is placed to indicate the point at which a restriction, requirement or prohibition begins or ends, it must be placed as near as practicable to that point."
The counter argument is: would it have made any difference if the signs were placed where they should have been?
One that could go either way depending on the adjudicator.