How to Approach This? With Pics

I've always used products such as gap filler for stuff like that and never had any probs with even bigger gaps. As long as you give it a good finish with a trowel or similar.
No more nails is also good for filling stuff like that up.
 
Screwfix do a decent enough caulk for under a squid. Job done.
 
If it's 30mm deep, I wouldn't use a squidgy sealant at all.
Use polyfilla (doesn't have to be real Polycell polyfilla). But don't try to do it all in one go, and leave it to dry properly between applications.
I'd probably do it in three applications, the last would just leave it proud of the wall, when dry you can sand it smooth very easily and it's ready for decorating.
Don't use silicone for sure - nothing will stick to it, and it probably won't stick to the dusty crack anyway.
 
don't use silicone sealant if you intend painting over it.

only a moron would combine the two.
 

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