Personally as there seems to be issues with bleeding the coolant properly, I would be inclined to think it would be a coolant issue.

If the block was cracked I would have though the coolant temps would sky rocket as soon as you boost the engine, not after repeated attempts.

You would also probably blow coolant out of the engine as the compression stroke would pressurise the coolant channels and force the coolant out.

From what I recall Dan hasnt had any coolant loss?

If the block was cracked I would seriously doubt the engine would be making good power, and I expect Dan would experience rough running.

Equally on that matter, I doubt its the HG as the engine wouldnt sound too go if this had failed?

Could something like the water pump have failed?

My old CRX siR had a similar issue, normal driving wasnt and issue unless it was sat in traffic

The water pump came out and the impellor on the water pump had badly corroded and the blades reduced to stumps.

Maybe inDans case he is getting restricted coolant flow?

So he isnt getting sufficient cooling which is proving and issue after repeat runs?