Nginx config for hosting two nested websites - nginx

Question

I am trying to write a Nginx config so that:
If the URL is exactly /Site/ it must serve C:\Site\index.html
If the URL is /Site/something/else it must serve C:\Site\something\else (fallback to index.html if it doesn't exists) BUT only if /something/ is different from /api/ and /dev/
If the URL is /Site/api/something/else it must redirect the exact request to another server otherserver/api/something/else
If the URL is exactly /Site/dev/ it must serve C:\Site-Dev\index.html
If the URL is /Site/dev/something/else it must serve C:\Site-Dev\something\else (fallback to index.html if it doesn't exists) BUT only if /something/ is different from /api/
If the URL is /Site/dev/api/something/else it must redirect the exact request to another server otherserverdev/api/something/else
So the key point here is that:
/Site/ and /Site/dev are two different websites
Each one has its own .../api endpoint
So far I wrote this config:
server {
listen 19001;
include mime.types;
location ^~ /Site/api/ {
proxy_pass http://otherserver;
}
location ^~ /Site/dev/api/ {
proxy_pass http://otherserverdev;
}
location = /Site/ {
root C:\Site;
try_files /index.html =404;
}
location ~ ^/Site/(.*) {
root C:\Site;
try_files $1 $1/ /index.html =404;
}
location = /Site/dev/ {
root C:\Site-Dev;
try_files /index.html =404;
}
location ~ ^/Site/dev/(.*) {
root C:\Site-Dev;
try_files $1 $1/ /index.html =404;
}
}
This doesn't work at all, I'm getting index.html in every request and also dev and nondev are mixed up.
Is there a way to achieve what I need?