I took the simplest approach I could and was able to find a solution that would work for me. I also have a TZO custom domain to make it easier for friend and family to find my server(s) and then as I mention I use my Primary WHS v1 Server to direct the traffic to my other servers using their subdomains and assigned port numbers. So it works like the example below:
http://CustomDomain.com ~ Brings you to my Primary WHS v1 Server which provides the links to the other servers
Link 1 Example:
https://Server1SubDomain.com:445 ~ Port Forward 445 to 443 to Reserved IP for Server 1
Link 2 Example:
https://Server2SubDomain.com:446 ~ Port Forward 446 to 443 to Reserved IP for Server 2
Link 3 Example:
http://CustomDomain.com:9080 ~ Port Forward to assigned server for Remote Potato
Link 4 Example:
http://CustomDomain.com:8079 ~ Port Forward to assigned Server for SubSonic
All the servers on my network have Reserved IP Numbers which makes port forwarding easier. To avoid certificate issues when using HTTPS I have used the Remote Access SubDomain name followed by the external port number assigned which then forwards the port to 443. However as I mentioned this doesn't work when doing it with the HP MediaSmart webpages which seem picky about 443 and attempting to resolve it internally in WHS offered some better results but I was never able to get it fully functional in a way to allow the MSS Media Streaming Functions to work properly.
In the end I actually considered it a waste of time for me because at the time I was already using SubSonic for Music and ORB for online video streaming. Today I use Remote Potato which replaced both but family members want to play music a certain way so I will be bringing back SubSonic. I also use Remote Potato for sharing Pictures and use the Whiist Add-In for WHS v1 to create picture webpages and to create the links to direct traffic on my Primary WHS v1 Server. Also I have to note the media functions both in HP MSS and WHS 2011 are limited so the software I mentioned above is more flexible and handles a wider range of file formats plus they simply work better.
Oh one more thing and that is I do not use nor require the use of any of the HP MSS WebPages. Everything I do is using the stock WHS v1 Web Pages. In doing this I also had to remove the logon button to elliminate the certificate error because on my Primary WHS v1 Server I use an external port xxx to internal port 443. So while the custom domain gets me there the actual Logon Button was using the SubDomain name and popped up a certificate error which was annoying so I chose to eliminate it and provide a proper link as shown in the examples above to correct the issue.
At first it really sounds confusing but its really a very simple method of manipulating ports to achieve a desired result. Using the custom domain simplifies the task of getting people to my server and the links there make it simple for everyone to access the other servers without having to bookmark them or remember rather long link addresses. So for all who use it everything is still point and click which keeps my intake of Advil to a minimum.