There have probably been more bad decisions made because "I've got to be back at work Monday morning" or "they're expecting us on the 14th" or similar schedule related pressures than any other reason.
I'll be delivering our new boat up from Long Beach to SF Bay here shortly which means we'll be rounding Pt.s Conception and Sur against the wind and waves in the winter. I've done this a few times in the past and I'm here to tell you the conditions can range from flat calm to uncomfortable to dangerous to outright impossible. You can bet that we'll be watching for a weather window to start on and if conditions deteriorate by the time we get out there, we'll hunker down for as long as it takes for things to settle down. Or even, give up and try again another time. I want to get the boat up there, but I'm not going to beat up my crew, my boat or myself to do it. Fortunately, there are some great places along the way to hide from the weather.
We also "plan" for 100 miles/day when on passages. When all things average out, it's been a good approximation of our actual progress. When doing coastal hopping (day sailing to about a week max), we're often guilty of firing up the diesel when the wind dies, usually so we can get in to where we want to stop before dark. During our offshore passages (we've done 3, the longest being 31 days) we normally don't (except for crossing the N. Pacific high, but that was planned).