Fixing a damp issue on Chimney Breast

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I have posted this on roofing forum so apologies for repost.
We have recently purchased a late Victorian end stone terrace property as our first home and are encountering lots of issues which is proving disheartening and costly!

We were aware of damp issues in the upstairs bedroom on the Chimney Breast which is on the top floor (attic is converted). We removed extensive amounts of ivy on the exterior wall to try and improve the issue as I know his can be a key factor in damp issues.

We have had the roof inspected and the flashing (which was missing), chimney pots reset and pointing repaired. We still have notable issues internally such as bubbling paint/plaster and discoloured walls.

We are now unsure whether this is due to the damaged plaster and moisture simply seeping or whether there is a more serious issue with penetrating damp. I have limited experience on this but the position of the chimney in relation to the roof pitch and wall may be a factor?

The wall is wet to touch and there is discolouring and flaking paint/plaster (see pictures).

I’m posting on here to try and get a steer from more experienced members as to whether this is simply a case of removing the plaster and waterproofing the wall or whether a more extensive external repair and roof is needed? (See image and dark wet patches on exterior wall)

I may look to get the roof looked at again (previous roofer was confident in repair and was the only one who actually got on the roof to look at it for his quote!)

Any help would be appreciated!
 

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Is the chimney capped and ventilated?
Internal photos, give no clue to the problem , require external.
 
Thanks for reply.

Chimney is capped but bottom has previously been stuffed up with rubbish (carrier bags etc). There are vents on each floor with now disused fireplaces.

I thought I had attached external image but please see below. On close inspection could it be pointing and mortar on external wall which could be an issue?
 

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Not my area of expertise, but as a decorator, I have come across hygro-scopic salts


A customer paid £20k to have his house repointed, thinking that the old pointing was responsible for the damp patches on a chimney breast in a loft room. After the pointer finished, I repainted the room (over easter). When winter rolled in, the same stains came back.

It was down to the salts in the old soot. They absorb moisture throughout the year and then dump it into the brickwork during the cold months.

The solution was to hack back the plaster and use sand and cement.
 
It could be damp/water penetrating faulty pointing, or salts trapped in brick and plaster as said
 
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