According to Huckel's rule Four Criteria for Aromaticity
The molecule needs to be (1) planar, (2) cyclic, (3) fully conjugated, and has (4) 4n+2 electrons.
Your molecule does not seem to be planar (b/c of N and O atoms) but assuming that it has a nearly planar conformation it satisfies all other criteria.
You only need to count one of Oxygen's lone pair and ...
No. The 6 membered ring is also a part of its aromaticity.
This can be better understood by considering the Zwitterion of Caffeine.
The entire molecule is planar, conjugated and has 10π electrons(4n+2)
Reference:Slides by Nevina Keskineva
Here is a proposed route starting from aniline.
First protect the -NH2 with t-BOC
Directed lithiation of t-BOC-aniline (sBuLi/Et2O, -75C) and quench with MeSSMe to install -SMe in the 2 position.
Directed lithiation under the same conditions quenching with Ethyl Chloroformate to install -CO2Et in the 6 position.
Oxidise the -SMe group to sulfoxide (MCPBA, ...