I've read through another similar post and thought I'd give this another try with a fresh question/post to see if someone at Samsung is even interested in resolving this issue, since many others are having the same problem that I am having.
Technical Background - I have 2 phones and 2 watches. I recently upgraded my phone from an S7Edge to a Note9 - and - I recently upgraded my Gear S3 watch to a Galaxy watch. (because when Samsung repaired it, they replaced the motherboard of the Gear S3 with a non-Verizon-compatible SIM - thank you very much Samsung!!!)
I have the newest and same version of Galaxy Wear running on both phones - and - I have the newest and same version of Galaxy Store running on both phones. The only difference right now is that my old S7Edge has a SIM card that's configured for ORANGE (French Telecom) currently running in Airplane mode. My Note9 is currently setup for Verizon. Both phones are logged onto my Samsung Store account.
PROBLEM - I was able to reinstall ALL of my paid for watch faces on my new Note9 phone using the steps that have been outlined in other posts - while running GEAR, open your Galaxy Store, click on the upper left 3 lines, click on My apps, click on watch. In the case of my Note9, all of my watch faces showed up and allowed me to reinstall onto my phone. However when I do this same set of steps for my older S7Edge (where coincidentally they were originally purchased on before my phone reset.) nada - blank - empty. I was able to download a free watch face into my older phone, but as for seeing faces I previously purchased, they are not there. It also doesn't matter if I turn on my SIM or not - I'm in the US, attached to my WiFi network with both phones.
It seems to me that this is a serious customer service issue if content that you're buying through Samsung cannot be easily restored on multiple devices. Since you can only use a watch face one at a time, you also wouldn't be violating software sharing policies. Lastly - I did try and uninstall a watch face on my Note9, but it still does not show up on my Edge7.
Given my previous less than stellar experience with Samsung, I'm really disappointed. It seems to me that more effort should go into resolving this issue if they want to retain customers buying their products.
I welcome all suggestions - but at this point, I'm not hopeful that there will be a resolution unless an update to their application occurs.