[quote=@Starlance]
Do you have a "current year" date in mind (Unless it's stated and I'm just blind)? Not super important I guess, but I like to have a fixed point to base the character's history on.
[/quote]

Update: I've added dates at various points into the opening post, with the current date being CE 2083 

[quote=@Letter Bee]
<Snipped quote by Starlance>

I like it, but it's up to Silverwind if she'll accept.
[/quote]

*He, but thank you (I think, haha). 
And yes, something like Starlance described would be perfectly acceptable. Similarly, something like having experience as a civilian pilot through a family business like a cargo ship and then joining the Resistance and doing flight training would work for a pilot of a younger age in the low 20's.