What's the best way to monitor a multi-port member?

We currently have 11 applications in tomcat that we want to put behind VirtualIPs so we can manage which member PORTS are down for migrations or issues since our service management software isn't smart enough to detect whether the tomcat port is active or not.

We have 8 environments and I was thinking I could make only 1 VIP per environment instead of 11 but using port "0 (any)" on both the Virtual and the Pool.

10.10.10.10:any
    1.1.1.1:any
    1.1.1.2:any
    1.1.1.3:any

app1 = 8443
app2 = 8543
app3 = 8643
appN = 8343+(100*N)

I want to monitor the application ports in such a way that ONLY the port for a specific app on a specific member is disabled. I understand how to down a member if any port is unavailable.

For example, if we are doing a migration on App1 is it possible to stop traffic to 1.1.1.1:8443 while still allowing traffic to other ports on 1.1.1.1?

My fall back in case this is not possible is to create 88 virtuals (one for each application/environment pair) and 8 more virtuals any time we add a new application.

Any hints on how to avoid this are greatly appreciated!