Had the chimney sweep at my place with cameras and the whole shebang for several hours now. Bottom line; the pipes run crisscross after all the years of changes in heating and ventilation. So the only way to figure out how to connect an upcoming pellet boiler is to dig into it and see how it looks in reality.

Is it just a matter of putting on the cowboy hat and grabbing the car hammer (with normal care, of course) or is there something to consider when going diagonally through half the chimney?

Any specific mortar and bricks to use when I rebuild it?
 
It sounds strange that the chimney sweep couldn't say more than that. For each channel, you can at least gauge the length. Instead of breaking apart too much, you could start by drilling a small hole with a hammer drill (around 6-8 mm) where you think there's a channel you want to use, and then investigate further with light (drop down a 100 W cord lamp into the channel and turn off all the lighting in the basement) or use a smoke grenade, seal at the top, and see if it seeps out in the hole. Or you could smoke a cigar and blow into the hole and have someone sniff the chimney on the roof. Yes, there are many ways. You should be able to map in a better way than starting to demolish everything. You build with whole bricks (not hollow) and C-mortar.
 
Sure, we've had fun with everything you've mentioned. The smoke test didn't reveal much, smoke came out of almost all pipes regardless of where we inserted the smoke cartridge ;D

The trick is, I have two channels to choose from:
- one likely (!) goes to two ventilation holes, one of which opens into the new boiler room and a soot hatch, all essentially as far apart from each other as they can be... We haven't managed to figure out where they connect to each other and how, the camera has only given clues and the plumb measurements don't match each other
- the other is probably the old pipe for the coke boiler that used to be in the house. It is currently sealed, and I can't access it in a reasonable way at the moment, there's an electric boiler, pipes etc in the way...

In short, I have to break it open to make a visual inspection to find out the truth.
 
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