All I know about it is that Optiboot determines the cause of the reset and acts accordingly. Software resets don't count as a reason to invoke the actual bootloading part.
Not forever. Older optiboots always had a delay. Maybe try one of those.
But westfw might have better ideas.
If you have a spare pin you could connect it to the Reset pin and set it to OUTPUT+LOW to force a hardware reset. When the reset happens the pin will revert to INPUT and the existing 10k pull-up will cancel the reset.