Crack in my chimney crown but new leak? - or is it condensation....

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Hi all, I joined specially to moan about my leaky extension....
So. Solid granite 1800s cottage, with I'm guessing Victorian/turn of the last century single storey pitched roof extension on the gable end/
When we moved in there were tiles missing off the extension roof and we had a complete new roof fitted to the extension, plus the chimney re-rendered. Water still getting in, so we had the roofer back - he reckoned the only place water could be coming in is round the bathroom windowsill, so he sealed that up.
In heavy rain with the wind coming from a certain direction, you can hear it coming in down the chimney breast (which is actually in the main bedroom, so you can imagine how that one goes) or if you're standing in the extension next to the chimney, you can hear it dripping overhead.
Been told by various builders and roofers the roof is sound, it's a) coming in through cracked render (been repainted over the summer with good quality masonry paint) b) definitely the bathroom windowsill (definitely isn't unless I'm imagining the sealant he put in that I can see out of the bathroom window) or c) needs a total rebuild of the chimney and drip trays putting in at rooftop level, happens all the time in Cornwall.

This is the crack on the chimney crown (...which was refurbished last March but I've had the roofer back that many times he's stopped talking to me) and where I think the bulk of the issue is.

I've now got a *second" leak on the roofline, at the other end of the building - it's a slow drip rather than an immediate trickle, and it's right below a missing slate barge-tile. Someone's coming out Monday to look at the roof, but is one of the barge-tiles missing likely to be causing any kind of significant leak? (The insurance assessor said it was mostly cosmetic and would wait till the weather improved!) EDIT: if I cover this hole temporarily, a shiny wet patch develops quickly which moves down the plasterboard tracking the batten. The fact that it's wet on the ceiling side makes me wonder if this is condensation rather than a leak, being caused by the hole in the plasterboard allowing the warm air in my dining room is meeting the cold slates?
 

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