As for the question that Douglas asked, about why we start the timing on the first inbound leg since we know we are going to need to adjust from there, I think the answer is: why would we wait to the second trip around before checking the inbound time? Even if we know the first trip around the pattern is going to require adjustments, why wait to the second trip around before figuring out what we are supposed to be adjusting? That just ensures that the first AND SECOND trips around the hold are probably going to be jacked up, instead of just the first.
If I could draw it out I'd probably convey what I'm saying better.
Direct entry for example, you can't take a time and it doesn't leave you hanging or less equipped for the hold.
My first established leg outbound is always going to be a minute, no matter how screwy my first inbound leg from a parallel or tear drop entry was. (I'm talking /A piston aircraft because that is what I know)
Parallel entry, I go out 1.5 minutes to help with the turn back inbound depending on the winds, so I wouldn't adjust my first outbound from the standard one minute from what I saw on my parallel inbound.
Teardrop: This one is pretty close, but I'm still going to go outbound for 1-minute on my first "established" outbound, just to keep things standard.
Am I still going to note the time the second hand is sweeping by when I get established inbound the first time? Yeah, I'm not stubborn, it is a habit, but I'm not going to adjust my hold or put much weight to it.
Basically my comment came from my students getting to the VOR from the first inbound and going, "shoot! I forgot to take a time!" So what? I want them taking times because they are thinking about how they need that time, not the 'cuz-that-is-what-you-do part of aviation.