Agreed that Barnsley town centre has been redeveloped recently and is looking good. It’s still not great for shopping, as it will always be in the shadow of Meadowhall (15 min on the train).
In your situation @SandyDunesCoffeeShack, if i did decide to go north, I’d consider Penistone. Market town 15 mins drive/5 mins on the train from Barnsley, but with it’s own busy community, indy cinema, library, cafes, a few independent shops and bars, biggish Tesco, GP, dentist, fudh n chips, a couple of small restaurants, always stuff going on at the community-owned leisure centre, surrounded by nice countryside, which is not-quite the Peak District etc. It has a sought after grammar school, so there are always families to keep the town buoyant.