Lots of good advice here.

As far as the application time frame, I agree with boiler, do it now. There should be an availability date there somewhere.
You'll have to repeat the process every January. They do like to see that you've been working on getting on with brown for some time, that's it's not a spur of the moment decision. So if you interview in '19 they'll know you had an application on file for at least two years..

Hopefully some mil folks will chime in. ..or search posts by SaltyDog here. (maybe even send a PM?) A great source of mil-to-ups info..

Thank you for your service and good luck!

PS. There's a EWR-ANC 76 flight, so it's an option if you get based in ANC. Generally speaking, the commute is MUCH more difficult than to any of the other domiciles. However, the lines are somewhat better. Not by much but typically only 1-2 flights a day/night.
Also, ANC based crew members are generally much better pilots! They're also better looking than the SDF riff-raff. Just a few things to consider.. ;-)

.