score:4
In order:
You might get lucky but that's not the way it's supposed to work for many reasons. And 3 months is ample time to apply for another visa. It's annoying but you should be able to reuse most of the documentation and probably won't need to go to another interview to enroll your biometrics (as they would be kept on file from the first application). The main issue is that you would have to pay the visa fee again and make one or two round-trips to the consulate. See also
Upvote:0
Just to clarify: Schengen visas have duration of stay, validity period, and number of entries.
So what you need is two entries, a relatively short duration, and a relatively long validity period. As Relaxed pointed out in his answer, the Netherlands is more likely to give you one entry and a short validity period unless you already have a history of frequent visits to Schengen.
If you do get such a visa, you have to watch the duration carefully. You would be allowed to spend all or most of your days on the first trip, but then you would have no days left for the second trip.
Upvote:1
They might, depending on your status in US and whether this is your first Shenghen visa (if not, this is much more likely). Make sure you made it very clear on the visa application, and show that you have means to return to US (i.e. you've a green card or visa which is not expired yet).
Yes, you can enter on 1st or 2nd, but you have to leave before Dec 3rd. This assumes you haven't used all your days on visa (it may be made valid for, for example, 10 days - and this is total for all entries, not per entry)