Yes. There is always time to take leave and the farther in advance someone knows about it, the better. The problem with something like a wedding is that you will most likely be arranging shit pretty far in advance, where as with your career you have no guarentee when you will be starting stuff. Even when you have a set date of starting something, that date is ALWAYS subject to change and usually will.
Yes Thanksgiving and Christmas are always good times to do things especially in the training command. Christmas will typically get you about a 2 week block leave time. The best answer I can give you is that once you are done with TBS and you report to MATSG in Pensacola, take leave then. Someone in the pipeline now will have to let us know about current wait times. But even when you are quick to start up, you typically will have about a month off between TBS/IFS and API.
It's not easy but it's doable. Yes you can take leave but with something like a wedding, you can't take the leave very far in advance. Tell your fiancee now, and many times afterwards that you will try but it's no guarentee. O yeh and tell her to get used to plenty of shit changing too.