Not sure what you mean by my endgame…if you mean the end result of my Economic Development Plans, then here’s what I think:

1. Gradually. Note that pretty much all of my plans include the development of finance and banking. With that will come an expansion of non-metallic financial instruments being used in the economy: letters of credit, banker’s drafts, cheques, and bank notes. It will take a while for these things to spread beyond the relatively narrow confines of the urban bourgeoisie, however, even with an active state promoting the use of them by making them legal tender for taxes, for example. 
2. Absolutely. Again, pretty much all of my plans involve expansion of commerce with Essos, albeit with a very keen eye toward climbing the value added ladder as quickly as possible. In the long run, it’s not good for Westeros to be a natural resources exporter only.