Damp old chimney (ed.)

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Hello,
I think I've read most of the chimney related threads on here but want to make sure the assumptions I've made on my own chimney are sound.
Bought a house six months ago and got it all replastered before we moved in. It was a job that needed doing and although it wasn't the number 1 priority, it made sense to do it while the house was empty.
During the heavy rain we've had over winter a damp patch appeared, dried out, then reappeared with more heavy rain. We've not had rain for a few days now so it seems the damp patch has become a stain. See photo, you can just about make out lighter staining where water had run vertically during very, very heavy rain.

Ultimately, the plan is to have the house re-roofed but ideally that job will wait for a few years. At that time I may consider removing the stack completely. The question now is, will removing the vegetation from the chimney, repointing and capping off solve the issue presented until such time as the whole roof can be redone?
Whilst the state of the chimney is clearly in need of repair, could it be that based on the positioning of the internal stain that guttering is the problem rather than chimney?
Once I've stopped the leak, rendering the gable end is next on the agenda. The rest of the house was done by the previous owners, presumably budget prevented them doing the gable wall.
 

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Nice roof garden. ;)
The back of the stack is a notorious area for leaks, especially if it's overgrown with vegetation.
By the time you've removed the vegetation, capped off, and repointed, you might as well remove the stack to below roof height.
The cost of the scaffolding, or other access, paid only once will more than cover any additional cost.
 
I think JohnD was suggesting there might be some value in salvaging the bricks.

also that the chimney, and hopefully the rest of the house, looks well built.

good bricks should not be rendered.

The front, and showy parts of a house, often used to be built to a more expensive standard to impress the neighbours.

I'd have thought the water was penetrating at the uphill side of the chimney, where there ought to be lead flashing to lead away the water that runs down the roof slope. probably also a buildup of dirt and vegetation round the back, holding water.
 
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