They choose routes according to the lowest metric at the end of the routes, and the table is processed from the bottom line to the top line.
For the second problem, a local domain should be running a WINS server... put that info in the Advanced TCP settings of any adapter on the WINS tab. (it's global, so if you put it in one they all see it.) You shouldn't need to be logged in the domain to use WINS. HOSTS and LMHOSTS go in the %windir%\system32\drivers\etc folder... look there and you should find some SAMple files.