"General Membership" speaking here (it's certainly not a metallurgists view)
Generally, I don't grind tools beyond the point where I can comfortably hold (or touch) them. For smaller tools, I tend to keep them in their holders (or grinding guide e.g. Diamond tooling) – which also helps keep the tool cool. But it's worth mentioning that I'm generally not in a hurry either
Grinding can be a 'forming/shaping' process (new tool – heavy/much grinding) but is more often just a 'touch-up' (existing tool – light grinding) where most clearance surfaces don't need touching. It helps if the same grinding set-ups can be repeated when doing this. When grinding, I find it generally easier do multiple tools in one session and at the same general settings. So I can cycle through the tools. I also often hone a tool to either get the edge I need or to touch a tool up and this is much more ad-hoc.
So to answer the question about 'dipping' – I normally do have a 'pot' (ice-cream box) with water in it and dip or drop tools into it – but I think the key thing is that if the tool is 'cool' enough to still hold or touch, then I don't believe that it will come to any harm by dipping. If the tool really sizzles (e.g. is too hot to handle) when dipped, then this could be a very different matter of course.
You asked about HSS Swarf but I also use carbon steel tooling and much more care (when grinding) is needed with these tools to prevent heat damage. HSS is pretty robust though.
Regards,
Ian T