Having two w-2s, stocks and 401ks and owning a house, at what point does one need Premier over Deluxe?

Depending on your tax situation if you have investments or rental properties, TurboTax Premier might be a better product for you. It includes all the features of TurboTax Deluxe and it offers Investment Income Reporting, including stocks, cryptocurrency, and other investments. Rental Property Income and Expense Management with detailed guidance for landlords.

Only income from the investment stock is a small dividend, as reinvesting is not an option with this stock. There is no rental income.

I would stick with Deluxe, at least to start.  If you run into a situation that Deluxe can't handle, you will be prompted to upgrade while working on your return.  

Thank you