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Backstop
I'm not sure it would fall under permitted development - outbuildings cannot be forward of the principal elevation.
If you go separated, I'd be worried about water & other crap finding it's way between the walls, never drying out, and being a nucleating point for damp & rot.
Brick lasts a lot longer that wood - If the brick decides to be a dick, the wood shed is likely to be the least of your concerns
Flashing is well within a DIYers locker - If you use hand tools to chase out the mortar, it's difficult to fuck up too much.
(To qualify that last statement - I'd happily go blundering in with lump hammer, cold chisel and a bucket of wishful thinking)