... a challenge to cross the line on starboard and therefore favouring the pin end hugely. Leading the parade along the line, in order, are Jim H, Uncle Al, Jim L, Mike Murto and Richard S. This shift means two things to Uncle Al:  1. he can safely tack to cross Jim L   2. port tack, as it now stands, will let you nearly lay the windward mark.  Other things being equal (e.g. wind strength across the course, current or lack thereof, etc.), it is always safer to take the longer tack first. To me, other things are nearly always equal and I therefore disregard those other things 99% of the time. The other 1% is when I am fairly certain that going against the odds will pay off, virtually always because I can see better breeze over where I would otherwise hesitate to go. Of course, sailboat racing being what it is, there are no guarantees, but more of this a couple of pics from now where I can use the illustration.
Here, Tony's countdown has reached one second to do, Al has put the helm down and, along with Richard J (yellow hull), is the first to ...

Jim H. has followed suit. Why does it pay to take the longer tack first, you may be wondering. This was an extreme shift and is thus very useful to illustrate what I mean. On a beat (and elsewhere) it is always wise to keep one's options open, i.e. the ability to usefully sail on either tack. Once you reach a lay line that ability has, barring an act of God, ended. When the beat becomes as skewed as this one suddenly has, both Jim (1066) and Al (3854) are either laying the windward mark or very close to it. Let us assume as a teaching point, that Jim is laying the mark. That means he is out of useful options since he cannot usefully tack to starboard. Here that will not bother Jim because he is in the lead.  But we are not always in the lead and our racing strategy has to assume we may well not be leading. Imagine for a moment that this is further into the beat and that a starboard boat now comes across and tacks. If he tacks in front of Al, Al can usefully tack to clear his air since he won't reach the lay line until he gets to where Jim is. If the starboard tacker goes across an sits on Jim, however, any time Jim spends on starboard is distance wasted since he was already laying the mark. And even in the reality of this situation, with no one able to come across and sit on Jim's wind, Al is still in good shape. Jim may have the lead right now, being more to windward than Al is ahead, but, other things being equal (here, both boats get the same wind strength and direction - which is never a given but deviations can't usually be planned for - trying to will drive you nuts - so it's best to ignore those random factors and stick to playing the odds), the wind can do one of three things: two of these will benefit Al and one will not benefit either boat:
1. the wind does not change direction > neither boat gains (assuming equal speed and pointing which we always have to do or strategy discussions become meaningless!)
2. the wind backs further and lifts both boats, let us say 10°. Usually this benefits the windward boat (Jim) as he lifts inside of Al. But here, Jim is already laying the mark so all this shift does for him is let him foot off a bit and gain a tiny bit of speed. Meanwhile that lift has enabled Al to lay the mark, quite possibly to overlay it, so that now Jim's windward lead has become useless and it is a foot race to the mark > advantage Al
3. the wind veers back towards its original direction and knocks both boats, let us say 15°. Such a shift always benefits the boat that is to leeward and ahead, in this case Al. Both boats should of course tack on the header. But fairly soon, Jim will reach the new (because of the shift!) port layline and have to tack back if he knows what's good for him. Depending on the magnitude of the shift, Al may have gained enough to cross Jim or at the very least should be able to throttle Jim with a nasty lee bow. Either way, Jim is now faced with the dilemma mentioned earlier. If he tacks to starboard off the layline, all the distance sailed on starboard is essentially wasted - except insofar as it clears his air > advantage Al
So this is why you sail the (appreciably!!) longer tack first, and in fact, every beat eventually degenerates into this kind of situation as we get close to one lay line or the other. It is best to keep the useful options intact by avoiding the lay lines as long as is reasonably feasible.
See also To Tack Or Not To Tack, That Is the Question