Least favorite is def Ash. We call them sticky. Same reason no one seems to like the Pin Oak. Make a pile of ash branches the try to pull it apart...not fun. The ice storm of '98 bout topped all of them and the resulting growth patterns are kooky. 90degree bends all over the place. They hit the chipper feed bar all the time. We have lots of ash...and we know we better get used to cutting them down, cause eab is on its way.
We usually do not make big piles of the branches when staging for chipping, like we would with White Pine. We consider White Pine slippery, with respect to branch on branch action. I really try to steer people from full canopy prunes on Ash. I have not meet a rewarding one yet. The fall foliage sucks. Do not know why anyone would ever plant one in a yard.
Thankfully no one has ever had us climb/prune a Black Locust. They are nasty.
We do not have many Pin Oaks. We got to prune the largest one around a few months ago. Yea, more time spent getting the cut branches out and down then cutting. No poison ivy. Still a very rewarding tree to prune.