Yeah I was at 82' and pulled a tape on the way down to cut exact 16'6" logs except the tree had a decent lean to it- made for a heck of a ride. I still want to know how big ya'll are taking stuff down on rope. it pretty much scares the crap out of me every time I have to block down logs 'cause I've never seen a tree break under a load and don't know what would do it.
Well I have seen trees fail; and years ago had one fail I was on (all be it failed because of a skidder pulling on it and not a chunk of wood dropping). I saw it coming, uncliped and jumped (was maybe 25 feet up and marshy ground so was lucky - ended up to my knees in mud crap but other than that ok).
Generally speaking a large tree can take a lot - think of the stress put on it when heavy wind blows crown around. But I have never seen any perfect science for it. A lot of factors; species; health of tree; etc.
Personally I would not try much more than you are dropping, half a ton (or slightly over) is a lot of wood. But you do need gear to handle it (and with a large safety margin).
Personally if you are dropping much of that sized wood; I would get a large DMM rigging block, a nylon sling rated at at least 12,000 lbs working load, 3/4" rope (what kind you using - I use Stable Braid for heavy loads) -- or even 1" if you can find it but watch rating as some 1" is less than 3/4" Stable Braid, and something heavier than porta-wrap at bottom.
Letting a piece run is not as difficult as it sounds, but start on smaller wood and work up with practice. Groundman is doing the work, and he needs practice. You need enough wraps on friction gear that they can stop the piece at will if needed; but few enough that if they let slack into the rope it will slide. Practice with very small pieces. Essentially when piece is dropped initially they let some slack go out into rope; will not go at full speed as friction gear will still slow down some; but it will be pulling rope as it goes. If done right, when they stop it there will have been a significant amount of deceleration in the piece instead of a sudden static stop at end of rope. The nice thing about heavy gear is you can actually take slack up in rope as the drop begins -- shortening the amount of actual fall before the deceleration begins (you can not do this with porty) and then it is easier to control run on bigger pieces. The Hobbs in a pure dead fall will handle more than the GRCS; but in real world scenerio with safety factors built in they are essentially the same for rigging. (each has pros and cons and followers) The idea in letting wood run; especially heavy wood or when in weaker tree is to reduce the shock load or impact at the stopping point. This takes a significant amount of strain off of all the gear (rope, block, sling, friction point, tree, etc) and takes the climber for a significantly less thrilling ride.
I have seen a lot of variables and different techniques used since I have been doing this (started in '74), some good, some bad.. some down right stupid. But personally I prefer to over rig and have a huge safety factor in the gear.
Watch your rope as well; letting run under those loads can cause a lot of heat, wear and stress on rope.. although static stops will cause different kinds of wear as well.