It's an overwhelming process, even if you know what you want. It's good that you've narrowed it down to exact procedure and surgeon though. I'm still struggling there for a lot of reasons.
As far as insurance, look through your school and see what options they have. A lot of student health insurance policies include a lot of trans stuff these days. If there aren't any options that work for you, look into plans offered by the Affordable Care Act. Go to
healthcare.gov and do a search. From there, you can figure out what you can pay per month and find a plan that maximizes the investment you'd be making in it.
I believe (not entirely sure, but fairly certain) that Crane will work with any insurer that covers the procedure, so as long as there are no exclusions you should be good. My plan in DC has no trans exclusions but didn't specifically list any kind of SRS, so I had to ask about it. They told me it falls under surgical coverage, and that medical necessity is based on whatever the surgeon requires to perform the procedure (so letters and length of time on hormones for Crane).
My plan actually involves going back to school for the benefit of deferring my student loans once I start the process. Ideally I'd like to have the first stage done in early/mid summer (2016 or 2017), start school in the fall, have the second stage done in December or January, go into the spring semester, and then finish it all up the following summer (I want MLD and it's 3 stages for sure). I think the only part that would be rough is coming back from surgery post-winter break, depending on when I have it done and if there are any complications. Hopefully I can have it done as early as possible in December so that I've got the majority of January to heal.
My advice would be to figure out Crane's timeline between procedures and see how it would slot into your school semesters. In my experience, grad school is the ideal time to be going through something like this. For one, you're more likely to have final papers or presentations than final exams in most classes. Professors are also a lot cooler about letting you take time off from class if you need to. My mom got sick at the beginning of December in the first year of my Master's, and my professors excused me from classes for those weeks. I turned in my final papers online and did a long distance Skype presentation in lieu of coming in.
Good luck as you start planning!