Sorry for the swarm of posts but I figured it out.
Hopefully this solution can help someone else down the road trying to do what I am doing.
The solution of my problem was to use VBScript to randomly generate a integer. The script is:
==============
Public Sub RandomVarGen
Randomize
Project.Variables.rand = CInt(Int((1000 - 1 + 1) * Rnd() + 1))
End Sub
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Changing the underlined 1000 to X, you can randomly generate an Integer X and assign it to the variable rand.
From here, I can assign my RowIndex for Table.Item to Project.Variables.rand and have a randomly generated RowIndex. So:
For those looking to randomly assign a value to a field:
1) Use the Data Generator to generate a table of strings that can be assigned to a field. Generate as many as needed.
2) Create a variable to store an integer
3) Create the script above
4) Before each random field, run the script
5) Use Project.Variables.[YourTableName].Item("[YourColumnName]", Project.Variables.[RandomVariableIntegerName]) as a code expression, assigned to the text property.
6) Enjoy.
Phew.