Leaking dormer window and council keeping me waiting.

andrew-b

Yep if it's facing the road then it's a planning issue. No doubt you'd get permission. Will it add value? Probably not. Will it make the property sell quicker? Possibly as flat roofs are infamous for problems and the pitched roof will add to the kerbside appeal.
I guess it comes down to money in the bank now and how long you see yourself living there. If your in it for the long haul a pitched roof now will work out cheaper than a new flat roof now and then another in 20 years time. How much is the planning permission going to cost though?