To the original post, first, a crane is like any other tool, use the right one for the job. I'll spec a bigger crane where necessary and work with an operator that isn't going to use shortcuts that may serve his agenda. Keeping the LMI clear is just part of doing tree work. Having to incur a cost for a repair is also part of the job. Where I'm uncertain about the overall weight of the limbs with foliage then its a matter of communicating with the operator.
The first pic is a test pic. It'll give you the weight for a given size of limb. What you can do is then superimpose that image in your head against the next pics until you get to the wood use the green log weight chart.
Sometimes it's hard to gauge strap placement. I'll ask my op if it looks set at the right point to keep it butt heavy and adjust accordingly. Your both on the hook for the outcomes of each pick so it's important that you're in agreement.
I've looked online to see if there's anything to show leaf weight to work up a better means of accurately estimating crown weight. There isn't yet and I suspect any would be cumbersome to use on the fly.
If your crane op isn't willing to work with you on building your skills and pushing for shortcuts that may put you at risk, find another one.