[Army to AF Transfer (Green to Blue)]

So you're only about 27 now? How far into your ADSO from West Point are you, 3 years? It looks like if you were to start talking to guard and reserve units about one year out from your release, then you should be fine to get out and report to UPT ASAP before you turn 30 (I reported 4 days before my 30th birthday!) It's a long shot but as you get closer and you find out you need to get out a bit early, a short polite email to the J-1's office (currently Brig Gen Margret Burcham http://www.jcs.mil/Directorates/J1|ManpowerandPersonnel.aspx) regarding your situation may be warranted, simply mentioning that the AF is short pilots and you would like to transfer ASAP, that could maybe trigger the office to talk to the Army's manpower and reserve affairs office to let you get out early. That's how I managed to get out in time to start flight school without a waiver but it was already after I was told I was accepted by a guard unit so I had a statement from them that I sent up along with my request, and that probably helped build my case. Doing anything like that now would probably be putting the cart before the horse. I managed to get 2 years off of my Army flight school ADSO, and I know another guy who got 1 year off of his but man that's rare, and I think the J-1 email and the fact that a unit was already willing to hire me made the case. I was also going to be 31 if I had to wait for my ADSO to end, and you'll only be 29.5 and won't even have to go to OTS first so they might not care and tell you to just wait and let the AF figure out how to get you into UPT in time.
Definitely take those tests sooner than later. I'm not 100% sure what the differences might be for someone who is already commissioned, but as as Warrant I had to take both of those tests in order to go to OTS. Not sure if you don't have to if you're already commissioned but they get pilot aptitude scores from both of them so I'd imagine you would still need to take them, if for no other reason than to show a guard or reserve unit's hiring board. They're not too bad but you should definitely get the study guides and take all the practice tests you can and time it. 
I'd say your time is something like:
Take the test and get as high a score as possible, I think they're good for 3 years so be sure to take them at an appropriate time.
Continue to build hours, preferably instrument time.
Volunteer for a full SERE-C course (you're going to hate me for recommending that but it'll help you get hired and get it out of the way nice and early while you're young). It's something you'll have to do anyway if you want to be an AF pilot and it's quality training. I think it has a year ADSO so the sooner the better.
Start talking to guard and reserve units (1-2 years from the end of your ADSO) about your situation and timeline and how they should be able to get you into UPT before you turn 30 if things are set up in advance but you'll probably need a commissioned service waiver (if over 5 years as a commissioned officer at the time of release) but those are easy to get, especially for heavy units.

Fantastic post man

[Army to AF Transfer (Green to Blue)]

I lurk on this thread occasionally and was wondering about this AF pilot shortage I have read about. I am a 32 year old Center Controller with the FAA and was/am a commissioned Black Hawk driver with 900 hours. Now in the IRR. Anyone with knowledge know if units are accepting age waivers?