Since your ACL and Security Group allow all outbound traffic, you can check the OS-level firewall to see if your windows resource is blocking requests. You can also enable VPC flow logs to have logs of all the requests leaving and coming into your VPC in order to have visuals if traffic is leaving instance or VPC and coming back.
Specifically had issues with returning ICMP traffic and HTTP return traffic, determined to be problem with dynamic ports. NACL Ingress rules added for ICMP and the Windows dynamic port range (49152-65535), thus enabling outbound traffic from the instance.
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