Like someone said above use TS Gateway, you can configure who can connect where they can connect to (In server 2008)
Id think that for a testing server your own certificate would be fine. The only problem with homebrew certificates is that they throw up errors for users as their browser cannot verify its validity (as its not from a trusted CA). This is fine for your use, or you could inform users that this will happen or buy one later on if the server becomes a production server for users.
Ive used IPSCA cert for my mailserver and it was free