I am using a camera connected directly to a monitor to reduce lag. This allows me to see both the monitor and the board at the same time, without moving my head. I see the board an the tip at an angle allowing me to judge the height. When soldering, I will mostly look at the monitor and regularly scanning to see the height of the tip.
The bigger problem is with placing fine components on the board. It's just slow and irritating. I will position the component in its location and then slowly bring it down until it touches the paste.