I'd take the second one as you start to come off the first.
BOOOO chasing! Never worked for me. If I'd try to re-up, as it were, I'd just waste the second batch. All at once was the way to go for me. But then that's why I stopped taking E. I needed at least 3 per night to get much effect at all. 4 or 5 was a better night. And that's just retarded.
Yeah I think if you wait too long it might be a waste, but for me it always worked best to take the second when you first started to feel yourself on the far side of the peak. Sure you might ride down a but before the second hits and you're wasting the second half of the effects-curve, but it lasts forever in me. If I take a pill at midnight, it's not going to be gone till 6-8 the next day. if I have two then I'm staying up two days like it or no. I'm usually too busy with my normal life to blow so much time. That's the biggest reason I'm so "cautious" with heavy drugs. I plan out each big event well in advance and schedule for it. I am really too busy to hang around in stupors or in post-ride recovery. I can't understand the 4-5 pills per night thing unless you're inherently tolerant to the effects, you're a heavy user, or you have cruddy gear. I've only ever had stuff that was low-grade once and that was a pathetic night. I thought it was just caffeine for quite a while. Then I thought it was speed. It turned out to be x, but so minimal I hardly felt anything. Last time I ever bought at an event.
I'm sure you have already, but just in case, read up on the stuff first, eitje. Best to know what you're getting into before getting into it. Especially note the contraindications and warnings. Hydrate yourself etc. Anyway, you know that. Have fun dude.
EDIT: As for skype, I may look into it at some point. If history is anything to go by, I usually wait until nobody is using a service before I join and then I'm left with all the hardcore junkies and I quickly learn to hate the service. That's how it worked with all chat services I joined, all online diaries, facebook, etc.