I currently have 1 line license with TTS (2 voices), if I upgrade to another line; the upgrade fee is only $300? Does that include a modem? Would I have to pay another fee for the TTS?
Yes, the upgrade fee is $300. It does not include modem.
The TTS you have supports multiple phone lines, so you don’t need to upgrade.
Could I run multiple list with different messages? e.g. list # 1 with 500 names with one message and list # 2 with 400 names and a totally different message?
Yes. You can create any number of call lists. Each call list is just a regular Windows file.
And, yes, you can also create different messages for different call list.
Is the maximum length of the Call/Phone list 1,000 names and numbers
No. You can set the length to any number.
Select Edit > Edit Options… from the program, set the Number of Rows.