Re: Mostly singlehanded...what lines should I run aft?
Lashing to the boom, day sailing or not, can cause issues that will also be much larger. The eyelets for the reef knots aren't reinforced in any way and can't handle any loads. Should your reefing clew line accidentally release you will destroy the sail.
I agree with you that if you are reefing for long periods of time that tidying up the bottom of the sail is good. However that barely fits under emergency reefing (the one time when having reefing gear in the cockpit is handy).
I don't see how the reefing hook holding down my reef cringle is any better than a piece of amsteel line holding down my reef cringle.
1986 Pearson 28-2 "Elena"