A bunch of the divergence from lore was done to spread out populated areas/balance/to help AI as I understand it but there's a bunch thats not great lorewise & this could be an opportunity to make improvements.
In the Eastern part of the Shire should be Buckland with capital Bucklebury & maybe Brandy Hall as a fort? (combined as a castle? It was notably fortified by Shire standards)
Moving East Staddle in lore is right next to Bree, there are also Archet & Combe close-by (could be farms/resources for Bree?)
I never felt happy about Barrow Downs being a populated town, probably should be just a couple of the new Ruins & make a couple of small towns elsewhere?
Bucklebury would contribute & maybe Archet/Combe, could probably still be spread out a bit but Staddle is too far from Bree currently.
I did find one map that puts a town named Andrath a bit South of the current Barrow Downs town. (just off the above map)
technically Andrath is just the name of the Greenway road between Barrow Downs & South Downs but if we do need a town in that area I think Andrath is a more acceptable name.