Well first rule of thumb is to remove exact ship dates because currently, you're violating all aspects of OPSEC!
Secondly and most importantly, slow down Highspeed. LOL Take it one day at a time and complete your initial training first. No one here can tell you when you will be completely done with training because first of all just because you got all of those options in your contract, doesn't mean anything unless you complete the training in schedule. Times and training dates change ALL the time for any number of reasons.
Regardless what you've read or what you "think" you know about Ranger training, you don't know. You go in there thinking you know what to expect and they will field strip down you regardless of how much of a "physical specimen" you were told you were. Some of the first guys to wash out are those that supposedly look the part and were told they would make it.
I work with and spend alot time with the Rangers, SF, "Contractors" and guys with "no names" here in Afghanistan at my FOB on a daily basis and some of the most Highspeed operators don't even look like they could make it through basic let alone Ranger and surely not SF training.
Based on over 20 years in the military;
First off, as an E-1, 2, or 3, you can't AFFORD to be married! Even if she can find a job, you can't afford it! If/when the babies come (and they will, usually at the worst possible time!), you REALLY can't afford it. As an E-4, maybe. As an E-5 and up, it becomes possible.
Check with your career counselor about assignments. You can ask for a specific assignment, but there is no guarantee you will get it. They WILL send you where they need you. Quite possibly, to a place where the name ends in -stan!
Also, check into what rank you have to hold to get transportation for dependents. I really doubt if the Army is going to pay for your wife to accompany you until you are at least E-4 over four years of service. I don't KNOW if it is still that way, but it was when I was on active duty.
As previously stated, as far as the military is concerned, a fiancee does not exist. Until you can bring that marriage license in, she is a non-person. She is not eligible for ANY benefits, period. You can, however, name her as beneficiary of your SGLI.
You really need to ask these questions of your Career Counselor. Regulations change frequently, and the military is trying to be more family friendly. It is very doubtful that you can find up-to-date information on an internet forum like this one. Very definitely do NOT go to anybody in authority (First Sergeant, Plattoon sergeant, Company Commander, etc.) and say "But I read on the 'net..."! They will very likely have unkind things to say about your gullibility!