Re: "Old Passwords: password I originally set up with. I've changed it so many times".
You might want to sign in to your Apple ID Account online and update anything that needs changing:
Eg: Check if the Watch is listed there ok, so you may use your current password,
Here's the link to Apple ID log-in:
https://appleid.apple.com
If needed: How to: Get a verification code and sign in with two-factor authentication - Apple Support
or
You could try the steps in this article:
If you forgot your Apple ID email address or phone number - Apple Support
and
If you forgot your Apple ID password - Apple Support
As it is a new iPhone to the Watch, this article has helpful tips:
How to pair your Apple Watch with a new iPhone - Apple Support