@logantate An update on this…
We purchased a paid plugin: WC Shop Sync Pro (Premium) from Wpexpertsio. The plugin didn’t initially solve the issue, but we have been working with the plugin developers to develop the multiple image sync feature. They currently have it in beta, which we are testing.
In the end though, the integration with Square is just completely clunky – there were so many workarounds we had to implement to make it work, that it became ridiculous.
We have elected to ditch WordPress altogether and go with the Square website builder. Whilst the Square website builder is extremely limited in design and features, at least it actually integrates properly with the Square inventory, which is the most important requirement for us.
It’s crazy to me that the third party plugin developer is more willing to respond on this issue than the official WooCommerce/Square plugin developer. Clearly it’s possible.