I have not used my twin headsails extensively and have only once been caught out leaving it a bit late in a rising wind.
I always furl the sails completely as the first step - I have never attempted to remove a pole with the sail still set.
I always lower the pole until the end is just below the height of the guardrail. So far I have managed to control it with the blue line, but if in doubt I put a fender on the guardrail as a cushion. This works for me but I admit that I have not had to try this in a heavy rolling sea where the pole end could catch in a wave top.
I believe there have been earlier posts on deploying poles, and there is a good description in the SM handbook of the whole process of setting and retrieving the twin headsails which I downloaded from the web-site.
Ian 'Ocean Hobo' SN 96