I teach contract drafting to third-year law students. It's hard work to take a complex if-then-else concept and render it in plain English.[a]
And here's the rub: Few clients want to pay lawyers to spend extra time on readability -- "good enough" (whatever that means) is the goal.
2. [EDITED TO ADD THIS:] It's not unusual for a private company's employee stock plan to include a "call" option that gives the employer the right to repurchase employee-owned shares when the employee leaves the company.
That makes sense when you think about it -- if you're a private company, you don't want a lot of random ex-employees owning dribs and drabs of your shares, especially if you're worried about the 500-shareholder limit (under current law).
On the other hand, for a company with an upcoming exit to buy back the shares at the employee's cost, instead of at a good-faith estimate of the stock's then-current value -- well, that does indeed seem unusual.
(EDIT: Some documents like this provide that, IF: The company wants to do its buy-back EITHER: (i) after an exit is announced, OR: (ii) if an exit is announced within 30 days or so after the employee's departure; THEN: The employee is entitled to the exit pricing for the buy-back.)
3. Again, not to defend Skype, but conceivably they might not have had a choice about the buy-back price, at least not without jeopardizing some kind of favorable income-tax treatment.
If I had to guess, I'd venture that, X number of years ago, some overzealous junior lawyer decided to draft the relevant documents so as to put the company in the strongest position s/he could. Now that zealousness may be tying their hands. I stress that I'm speculating here.
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[a] If you have occasion to write a complex if-then-else sentence, try using all-caps and punctuation like this: IF: It rains at least one inch today but not more than two inches; AND: It doesn't rain tomorrow; THEN: You will turn on the sprinkler system tomorrow; AND: You will not do so the day after.