Do you have InDesign and a spreadsheet program (Excel or Numbers)? If so, place the AI file onto a master page in InDesign and, while still on the master page, format a number in a text frame until it looks right. Make the text frame tall enough for only one line of text at that size. Delete the text but keep the text frame. Go to page 1.
Use your spreadsheet program to generate a column of numbers from 1 to 300, then export that as a text file. Now place that file into InDesign and hold Shift as you click on the text frame on page 1. All 300 numbers will pour in creating 300 pages. Export a PDF or print as needed.
The SerialNumbers script populates a selected textFrame with a sequential list of paragraph-delimited numbers with or without a prefix:
The NumberedCallouts script creates additional sequentially-numbered individual textframes, styled like the original:
To semi-automate production of a set of highly-stylized sequentially-numbered text objects, the SerialNumbers script can be used in conjunction with the TextVariablesFTROU script described here to create Variables Palette DataSets that can then be batch printed or exported.