help troublshooting or reconfiguring an irule

Will I have to install the cert/key pair on F5 as well?yes, you should import certificate and key from server to bigip and set it in clientssl profile. you are able to use default clientssl profile but user will get certificate warning page when accessing https virtual server.

And if so, I assume I can use the default server profile 'server-sslinsecure-compatible'?yes, you can use default serverssl-insecure-compatible on server-side i.e. custom clientssl profile on client-side and default serverssl-insecure-compatible on server-side.

And that will not interfere with my enterprise vault pool listening on port 80.not really sure if i understand correctly. anyway, i understand there are 2 pools; exchange pool is listening on port 80 and 443 and enterprisevault is on port 80. you have 2 virtual servers but same virtual address; one is on port 80 and the other one is on port 443, and you want to direct traffic to pool based on url.

so, i think configuration may look like this.

[root@ve10:Active] config  b virtual bar80 list
virtual bar80 {
   destination 172.28.19.79:80
   ip protocol 6
   rules myrule80
   profiles {
      http {}
      tcp {}
   }
}
[root@ve10:Active] config  b rule myrule80 list
rule myrule80 {
   when HTTP_REQUEST {
   if { [string tolower [HTTP::uri]] contains "enterprisevault" }{
      HTTP::redirect "https://[HTTP::host]/enterprisevault"
   } elseif { [HTTP::uri] equals "/" }{
      HTTP::redirect "https://[HTTP::host]/owa"
   }
}
}

[root@ve10:Active] config  b virtual bar443 list
virtual bar443 {
   snat automap
   destination 172.28.19.79:443
   ip protocol 6
   rules myrule443
   profiles {
      clientssl {
         clientside
      }
      http {}
      serverssl {
         serverside
      }
      tcp {}
   }
}
[root@ve10:Active] config  b rule myrule443 list
rule myrule443 {
   when HTTP_REQUEST {
   if { [string tolower [HTTP::uri]] equals "/enterprisevault" } {
      SSL::disable serverside
      pool foo80
   } else {
      pool foo443
   }
}
}
[root@ve10:Active] config  b pool foo80 list
pool foo80 {
   members 200.200.200.101:80 {}
}
[root@ve10:Active] config  b pool foo443 list
pool foo443 {
   members 200.200.200.101:443 {}
}