I have a customer that currently has 5 users internally. This could double in a few months, that is why I am trying to figure out the best solution. The current users go to cleints and web in currently to a W2K terminal server via Watchguard VPN using SSL. We also have a couple of users, with three screens, that use both their local desktop and terminal services internally on a regular bases. The applications running on the teminal server are mainly various, at least 5, years of Quickbooks and Office 2003. The also have the same setup at there local computers. All data is stored on a seperate W2K server that is the DC. I plan to copy this scenario so, we have purchase SBS 2011 Standard because we want to bring our email inhouse and also us it as data storage. We also purchase a 2008 RS server which I currently am configuring for terminal service (Remote Host, whatever). I have joined the terminal server to the SBS and can see it in RWW. However I am looking at my choice on the terminal server and wandering which route would be best.
I plan to have the Remote desktop Licensing on the terminal server. But I am wandering, would it be better to use RWW on the SBS to connect to the terminal server? Would this work? The easier solution, but I see multi logins to get to terminal server.
Or would it be better to install Remote Desktop Gateway and Remote Desktop Web Access on the 2008 R2 and let the users come directly into the Terminal server using the Web Access SSL? If so, do I need 2 certificates and 2 dns entries, I.E., remote.domain.com for SBS RWW and terminal.domain.com for the terminal server? I have multi outside IP's and I can configure the router so each can come over its own pipe.