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@FridayMarch26th
I'd definitely recommend heading out of Edinburgh through Inverleithen, I've tried a few routes in and out of Edinburgh from the South and it's the prettiest of them.
If you do Hexham to Ripon (mebe hop over the A66 and into Richmond) then you'll probably hit Harrogate shortly after. Heading South out of Harrogate you'll see Weeton's deli on your left hand side (it's big and pale green, you can't miss it). Stop there for snacks.
I don't know if Sheffield is a rough waypoint, or a specific destination, but I'd probably avoid it unless you've a good reason not to. I reckon you'd have an easier time sticking further East.