Your confusion is totally understandable. Making it more difficult to understand, both instructions are actually fine -- you can open the sealed container 14 days after pitching yeast, as the ferment should be done. You can also open the sealed container 15 days after hitting 1.010.
What is happening is the wine is undergoing Extended Maceration (EM), in which the post-fermentation the pomace (skin & pulp) soaks in the wine to extract more "stuff" from it. Sealing the container at 1.010 ensures there is activity, which produces CO2, which pushes out the air in the fermenter, making a safe (little or no O2) environment in which the fermentation completes, and the EM proceeds without danger of oxidation.
Typically, fermentation takes about a week, so the first instruction allows for an additional ~2 weeks of EM. The second instruction allows for ~1 week of EM. Some folks do EM for 6 or even 8 weeks, so 1 or 2 weeks of EM is fine. Let your personal schedule decide how long to do it.
@Matteo_Lahm, if it hasn't already been addressed, this points out a glitch in the instructions.
This is not the first time it's occurred to me that the kit vendors would all be doing themselves a tremendous business service if they assigned someone to watch WMT the way Matteo & Matt do. I've read these instructions several times, and my mind just glossed over the glitch.
Definitely squeeze the skins afterward. I made a pair of triple batches, and netted about 1.5 liters of wine by pressing the skinpacks.
Regarding re-use? There's not much left in the skins, especially after a week or 2 of EM, so it's probably not worth it.
An interesting experiment would be to make 2 identical batches -- one having the skin packs from a previous batch added. While I don't expect to see much (if any) difference, I may be wrong.