2 x core set
2x x-wing pack
1x tie fighter pack
2 x tie advanced pack
1x y-wing pack
This is exactly what I intend on ordering for the first wave. 2 Starters for the dice templates and core X's and TIE's. And at least one of every expansion, doubling up on the ships I want pairs of.
Next wave, I'll probably take a pair of each fighter and one each of the Mediums. The Interceptors are my favorite TIE, so Might end up with 4 before the third wave hits, whatever that may bring.
As far as pilots and upgrades, you will never have a problem running named characters and not having enough of the generic pilots as every ship comes with a selection of the generics. The TIE's actually have 3 generics each. So don't worry about pilots.
Seems several of the skill upgrade cards are duplicated in different expansions and the starter so that shouldn't be a problem getting most or all of the ones you need. And each ship expansion comes with the secondary weapon card(s) that it's allowed to use. In the end each expansion will have all the typical generics for the ship as well as a pair of named pilots and maybe one unique upgrade (droids and skills being the most variable). You'll always have enough torpedoes, missiles, cannons to go around. And probably plenty or droids and skills.
One thing of note, very few TIE pilots can actually take Elite skill upgrades. The named pilots tend to have a built-in special skill and no upgrade options. However the Black Squadron generic pilot can take one where none of the Rebel generics can.