Re: DDW and bailing out
I too endorse the "chicken (non-) jibe wholeheartedly, whether you are running out of searoom or not. Sea story follows:
Decades ago Marblehead Town Class sloops (17', spruce mast, lowers but no backstay, big main) during Race Week, and (surprisingly) found myself in the lead heading for the gotta-jibe-it reach mark as a squall overtook us. I "ain't givin up the lead" , so tried to jibe, I really did, but couldn't physically pull the mainsheet in to pre-trim the main for the jibe. Despite being much younger and bulletproof then, I took this as a sign from God that I had to swallow my pride, sail past the mark some, then chicken-jibe it. I seemed to take forever, and my 10-boatlength lead was down to two as the second boat, sensing victory, jibed...
and broke his mast in two places. Third-place and I think all others too (I didn't look back, had my hands full as it was really honking out) chicken-jibed. I did hang on to win that race, and was thanked by quite a few at the cocktail party for "chickening out"
To finish answering your question though, if I knew I was going to run short of depth or room, I might have rounded up earlier, dropped the main, and continued with just jib, which is much easier to wrestle down on a run.