Bit harsh on Chester, it’s not exactly miles from the centre!
City Road in Chester has improved in recent years with some decent bars, micropub and restaurants en-route to the City Centre, although the subway at the top of City Road is pretty off putting.
There are frequent buses from outside the station to the Frodsham Street in the City Centre but I don’t think PlusBus tickets are accepted? I presume ENCTS passes are valid? but not Welsh ones obviously!
If ever a railway station was crying out for a York or Sheffield style micropub then Chester would win hands down!
You're right, the 'dedicated' City Rail Link, operated by Aintree, doesn't accept PlusBus - in fact, I'm pretty sure it's just Cash (£1 Single) or ENCTS.
PlusBus (and other payment methods) can be used on Stagecoach and Arriva services between the Railway Station, Bus Interchange and City Centre (1 / 5 to Wrexham, 1 / X1 to Liverpool and 4 / X4 to Mold spring to mind).
The City Rail Link used to be free of charge and was funded jointly by all the TOCs that served Chester, and as I recall, was quite well-used back then.
As for York, I know they are or were thinking about building a bus station, but the thing is most of the services in York are locals and do a bit of a city centre loop anyway, so the clusters of stops around the Station, Piccadilly / Merchantgate and The Stonebow I think do the job. The only 'terminating' buses really are those to Leeds, Selby and Hull. The main issue with York is the terrible congestion.
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