The medical will be the biggest hangup right now as NAMI claimed they're months behind. You need to get a flight phys scheduled, and your shipboard IDC (if you're on a small boy) might not be too familiar with it. I'd recommend contacting the nearest medical clinic with a flight surgeon directly and asking them how you can make it happen.
You will have to wait until November as you missed the submission deadline for this board...but it also gives you time to get the medical shit done...barely. I had my flight phys done last Nov, various people fucking sat on it, as a result didn't get a response from NAMI until this May.
If you don't have a medical clearance memo from NAMI by the time the board meets, they won't even give you a look.
ASTB is easy, just figure out where you can take it convenient to you and hook it up...you're an active duty commissioned officer, so you can cut past some of the bullshit if you want to press the issue.
Go to the BUPERS website, search around for lat transfer, check previous boards to see what your FY group's numbers are. I don't think FY 09 has anything yet, but once they come out, you need to look at # of transfers allowed OUT of SWO for that FY group, and look at Pilot or NFO transfers allowed IN for that FY group.
You can put in requesting a waiver for the 2 year mark crap, and if you don't get it, just put in for the next board...your medical will be good for one year, so it's a paperwork drill of just changing dates from there. As for chances, the gouge I got from the PERS folks (who you should contact directly for current info) was that it's rare, but if the numbers/demand support, they can make it happen.
Also talk to your CO (at a minimum). You will need a letter of endorsement from him/her, so make sure the CO knows it's coming and is cool with it.