AirDrop Not Working When Signed Into iCloud
I finally found a solution that worked for me. This seems unrelated but it definitely was my issue. It also fixed my issue with Apple Watch not being able to unlock my Mac. Below is what worked for me.

On your Mac:


Open up Messages App
Go to Messages > Preferences
Select Accounts Tab
Select Blocked Tab
Locate and delete any instances of your own phone number and/or email addresses
Close and wait ~5 minutes for iCloud to sync the changes across all your devices


On IOS:


Go to Settings -> Messages -> Blocked
Same as step 5 and 6 above


After performing those steps Airdrop worked perfectly across all devices and, as a bonus, I was able to unlock my Mac with my Apple Watch again (I was previously getting "your mac was unable to communicate with your apple watch" error / "IDS device not cloud paired").

Hope this helps others!