So I finally got it set up after a brute force attempt. I have to say I was nervous even adding any money to it given all the issues.
1) Got the prompt on my ipad that Apple Pay Cash was available, but my debit card didn't / wouldn't show on my ipad.
2) Checked iphone, still no prompt for Apple Pay Cash.
3) Signed out of iCloud for the second time (I know, I have problems, I just can't leave stuff alone).
4) Turned off the phone for about 10 minutes and restarted.
5) All cards removed from Apple Pay on both phone and Apple Watch.
6) Tried to add back cards, but only a couple would activate on iPhone and none would activate on Apple Watch.
7) Tried removing cards and re-adding them.
8) No cards could be added due to "unavailable" error.
9) Had to go through all settings on the phone to make sure everything related to iCloud was set up (and it wasn't), re-enabled iCloud for Messages, Facetime, etc. Even My Card in contacts was wrong.
10) Made a bowl of ice cream and gave up for the night.
11) Tried to re-add all cards again this morning. Everything is now up and running on all devices.
Advice, just wait for these issues to get fixed. All this reminds me of why I switched from Windows back in the 90's, constant debugging, re-installing, fixing drivers. And don't sign out of iCloud unless you really want this working now.