Hello MakeItWorkPlease,
If it seems that the device isn't being detected when trying to use AirDrop be sure to check and see if the firewall or any other security software is enabled on the Mac. This page can help provide details on the firewall: Block connections to your Mac with a firewall - Apple Support
Similarly, check for any VPNs installed on either device in use, or if there's a profile/Mobile Device Management installed on them. On iOS these are found in Settings > General > VPN & Device Management. If any are installed try temporarily uninstalling them to see if they may be conflicting.
Also ensure each device has Wi-Fi and Bluetooth enabled, Personal Hotspot is disabled, the devices are within Bluetooth range of each other, and both devices are awake.
On the Mac you may also try setting up a new Admin account, switch to that newly created account for a moment, and see if it persists there. That can help to see if it's a system-wide issue or specific to the current account. If needed this page has steps on setting up the new user: Add a user or group on Mac - Apple Support
Cheers.