It is possible to have your server automatically log itself in when turned on.
This would allow you to put the dialup in the starup folder and it will run every time the box is turned on.
The basics are steps are as follows: (from technet)
To enable automatically logon, do the following:
Start Regedt32.exe, and then locate the following registry subkey:
HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\WindowsNT\CurrentVersion\Winlogon
Using your account name and password, double-clickthe DefaultUserName entry, type your user name, and then click OK.
Double-click the DefaultPassword entry, type your password, and then click OK.
NOTE: If the DefaultPassword value does not exist, follow these steps:
Click Add Value onthe Edit menu.
In the Value Name box, type DefaultPassword, and then click REG_SZ for the Data Type
Type your password in the String box, and then save your changes.
Also, if no DefaultPassword string is specified, Windows automatically changes the value of the AutoAdminLogon key from 1 (true) to 0 (false), which disables the AutoAdminLogon feature.
Click Add Value on the Edit menu, enter AutoAdminLogon in the Value Name box, and then click REG_SZ for the Data Type.
Type 1 in the String box, and then save your changes.
Quit Regedt32.
Click Start, click Shutdown, and then click OK to turn off your computer.
Restart your computer and Windows. You are now able to log on automatically.
NOTE: To bypass the AutoAdminLogon process, and to log on as a different user, hold down the SHIFT key after you log off or after Windows restarts.