It is not round robin. There is always a BEST route. If there are mulitple default gateways it selects the best one based on metric. How the metric values are assigned varies a bit by OS so I can't say. You generally do not want to rely on tie breakers, it is recommended that only 1 gateway exist. The OS does not know anything about other machines unless you tell it via static routes.
This is why in complex installation routing protocols are used, but it is rare to run a routing protocol on a end device.
If that's the case the second static IP should be checked on both networks, no? when i run a tracert on the static machines it cant reach, its seems to only try on the second network:
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NOT WORKING
C:\>tracert 10.11.0.1
Tracing route to [10.11.0.1] over a maximum of 30 hops:
1 <1 ms <1 ms <1 ms Router2 [192.168.2.1]
2 <1 ms <1 ms <1 ms [MY PUIBLIC IP]
3 * * * Request timed out.
4 * * * Request timed out.
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WORKING
C:\>tracert 10.10.0.1
Tracing route to 10.10.0.1 over a maximum of 30 hops
1 <1 ms <1 ms <1 ms Router1 [192.168.1.1]
2 9 ms 4 ms 7 ms 10.10.0.1
Trace complete.
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any idea what could be causing my problem? im out of guesses if its not the default handling. If i unplug my second connection, i am able to connect to both static machines without issue.