how do you itemize expenses for two separate side business with self-employed?
After you have entered first business and all of those expenses, go to top right corner to search box.
Type in either "business expenses" or "Schedule c" and hit enter and click on "jump to xxx" when it appears in results. That will take you back to your "Self-employed work summary" page.
There you will just click on "Add another line of work" and enter your second business and all of it's expenses.