Im a caregiver and own a medical marijuana dispensary should i keep these seperated under work summary or all under the same category?

You need to keep these as separate businesses.  They are not in the same category.  You will report your income and expenses for each business on separate Schedule C Profit or Loss from Business.

To enter your self-employment in TurboTax follow these steps:

1. Open or continue your return
2. Search for schedule c and click the Jump to link in the search results
3. Answer Yes to Did you have any self-employment income or expenses?
4. If you've already entered self-employment work and need to enter more, select Add another line of work
5. Follow the on-screen instructions to add your self-employment information.