The application process was not too difficult - I had someone in my med school's office who has been great in communicating with me in a timely manner about what materials she's received, what she needed, etc. If I had been back in the states, it would have been no problem at all - from overseas, it just took some advance planning to account for all of the delays.
The interviewing circuit was a little nerve racking since I had to block all of my interviews within the 3wk period when I was going to be back in the states. Trying to get all of the programs to offer you spots during that period was tough but not impossible. I actually said in the last paragraph of my application's personal statement that if you wish to interview me I will only be available for the first 3 weeks of December - no earlier & no later. I wasn't sure about putting that in, but it all worked out well & I got the interviews I wanted. The blizzard in the Northeast almost wiped out my interviews - but you can't predict or plan for that.
I think a single tour out in the fleet prepares you well for going back into residency - anything more & I think your skills/knowledge start to wane from being away from academic medicine for so long. I've had nothing but favorable feedback from all of the ER folks that I've interviewed with - both regarding my application & other military folks who've come back to do their programs in the past.
The length of your tour will depend on a couple factors: which flight surgeon class you go into (summer/fall/winter), whether you go accompanied/unaccompanied, and whether you're going to a follow-on FS tour vs. going back to residency.
All accompanied tours are a base-line of 3yrs, while unaccompanied tours are 2yrs (with a couple of 1yr exceptions).
If you're going to follow your FS tour with another FS tour, you will leave at the scheduled end of your tour....if you arrived in April 2002, you'd leave in April 2004. If you're going into residency, they'll extend you at that command until it's time to PCS/separate for residency...arrive in April 2002, due to leave in April 2004, extended there until June 2004 when you leave for residency.
The class in which you start can effect how much you may have to extend in your FS billet. Summer class (July-Jan) will put you into your FS tour in Jan/Feb, so you might have to extend 5 months there to get back in cycle with residency. Fall class (Sep-Mar) puts you in FS billet in April (which is me), so I've extended a couple months. Winter class (Dec-May) will put you to your FS billet in May/June - no delay to get into cycle at the end of your tour.
Hope I answered some of your questions. Feel free to ask if anything else needs clarification