I admire you for using QuickBooks Online (QBO), @bohtie.

I'll go over some specifics about upgrading your plan. If you upgrade your QBO plan to a higher version, you'll lose the discount on your previous plan.

As a way around, you can avail the 30-day free trial of the Essential version and import your data. This way, you can keep the discount privilege of your QBO account. Once done, you can export your data and import it back to your Simple Start version. 

Let me show you how:

1. Log in to your QBO.
2. Go to the Gear icon and select Export Data.
3. On the Reports tab, set the date range.
4. Add or remove items from the Reports and Lists tabs by toggling the slider.
5. Select Export to Excel.

You can also see this article for more details: Export reports, lists, and other data from QuickBooks Online.

Then to import them to the Essential version:

1. Sign up for free and use the same login credentials to easily switch between accounts.
2. Go to the Gear icon and select Import data.
3. Select the type of data you want to import.
4. Follow the onscreen steps to finish the process.

I got you this article with all the details: Common questions about importing data to QuickBooks Online.

When you're finished, you might want to look into this resource to help you modify your reports based on the data you require: Customize reports in QuickBooks Online.

If you have any further questions about migrating your data in QBO, please let me know. It is always my pleasure to assist. Keep safe and have a great weekend!