How tough is it to get new ships? I'm just wondering if the running joke prior to launch of ship makers having to make 1500 A-Wings to get to the next crafting level was remotely close to the truth.

No they dont have to make a zillion ships, just a zillion ship parts. There are several ways to customize your ship; Reactor, Engine, Shields, Armor(Front and Back), Capacitor, Droid INterface, Weapons, Defensive Weapons, and probably one or 2 others Ive forgotten.
I havent looked at the ShipWright class yet(might go that route with one of my guild's 'group' players), but the way theyve set it up is very similar to all the otehr classes. At the lowest lvl of Pilot, you can only use the lower end components; as you gain XP you are 'certified' to use higher end stuff.
One twist that Im not sure why they implemented(doesnt bother me really, Im just curious why they did it) is this: you buy a blueprint of a ship chassis(A-Wing, YT-1300, etc.) from another player(shipwright), but you dont actually get the ship from them. You have to goto an NPC Ship Chassis Dealer and pay them a not so nominal fee(I paid that fool 15K for my Kimogila class fighter, and that's available at the 2nd lvl) to turn the blueprint into a ship.
Pretty cool game though, and *for me* it's enough fun to get me back into SW:G. Dunno for how long...but Im definitley having fun.