Here's the scenario. Before the start in Tacticat it looks like the wind is stronger on the left side of the course. You read Tillerman's Tacticat Tip #2 Watch the Wind and so you decide to start near the pin end of the line. You get a good start but boats to the left and right of you get slightly better ones. As you head out to the left side of the course you never extend far enough ahead of the boats to windward of you to be able to tack and cross them safely.
Now you're starting to approach the port tack layline and still you can't tack. Maybe you start sending messages to that boat on your hip...
Eventually he gets the message. He and the six boats to windward of him flop over on to port, but by now you are on the layline, or perhaps even above it. Worse, it turns out that there was some decent pressure on the right too and some of the boats that went right are going to cross you. There are already fifteen boats lined up on the starboard tack layline and you can't see any gaps in the line.
Now you're approaching the mark.You can't tack inside the starboard tackers; they are too close to the mark. What are you going to do? Bear off and duck a dozen or more boats? Sheet out and wait? There are boats ahead of you on starboard. There are boats to leeward of you. There's nowhere to go. You're screwed.
So how do you deal with this situation and get around the mark cleanly and still be up with the leaders? Beats me. Basically you can't get there from here. I guess you should have anticipated the problem earlier and maybe slowed down earlier so you could tack on to port, duck some transoms and get into the starboard tack parade before all the gaps filled up.
If it makes you feel any better this happens to top sailors too. Check out this Monday Morning Tactician tale from CampbellSailing.com. Andrew thought he had an opportunity to round the mark with the leaders but ran into extra complications caused when another port tacker stole a late inside overlap.
Diagram stolen shamelessly from CampbellSailing.com.