I believe there is a thread somewhere on how to measure height using a stick.
You can invest in a clinometer and tape if you plan to do a lot of it. A clinometer measures angles. You go out say 100 feet, staying level with the base of the tree, take the clinometer and read the percent slope to the top of the tree, read percent slope to the bottom or stump height, then add the two readings and that'll get you the height. If the stump reading is a positive, or uphill a bit from you, you SUBTRACT that for total height.
There are many instruments to measure height-- they get pretty expensive.
After you figure the height of a tree or two, you can compare others in the area to those and estimate the height.
Usable height? Measure up to where you'll stop cutting or where the tree will break up at.
Another method, that I use for a quick timber cruise, is to envision a loaded log truck. How much room on that truck would your trees use? Around here, a log truck holds about 10 cords. This works well for blowdown.
Timber cruising is measuring and getting an estimate of the volume of timber.
Hope this isn't too confusing.