Car42ze
Why would you disconnect the headset before the two bar? As a standard safety procedure I disconnect headset only after two bar and tug a clear of the nose gear area then and only then pull the steering lockout pin after clearance has been given from the flight deck.
1. The lead should be long enough. If it isn't get a new lead.
2. We have a three people on the push back. Driver, headset man and assistant to handle tow bar.
Unless it's a towbarless tug in which case only two are required, driver and headset.