Bob, welcome to GolfClubAtlas! It's great to have you here. I've been a member at Flossmoor since 2014, and we miss you!
In my opinion, the 6th hole is the worst hole on the course--probably by a wide margin. It's a ~430 yard dogleg right. The fairway is relatively narrow, and there are large oak trees that overhanging the right side of the hole. So much so that you'd typically rather be in the left rough than anywhere on the right half of the fairway. But you can't go too far left because the out of bounds line is 10-15 paces away from the left edge of the fairway.
It's just a very awkward hole with very little margin for error and not much strategy of interest. When I play the hole in competition, I typically hit a three wood off the tee. If I'm lucky enough to end up on the left side of the fairway, I might have an interesting mid-iron shot into the green (although the fairway slopes right to left so you might still have to play a hold-off cut to avoid the oak trees). If I'm in the right side of the fairway, I might have to hit a big slice with another three wood to try to get it close to the green in two shots.
The green and the surrounding bunkers are interesting, so it could be a good hole, but we would have to tear down those trees and reconfigure the fairway somewhat. The new owners have some good changes in the works, and the 6th is surely one of the places where they'll get the biggest bang for their buck. I'm eager to see what they do with it.
Steve, it's great to hear your thoughts. I agree that the wooded area around 6, 7, and 8 has a different feel than the rest of the course. Old drawings and aerials suggest that a lot of those trees were there from the beginning, so that part of the course always had a somewhat distinct feel. One thing that made that section feel even more disjointed was the decision to move the tee on 7. That hole was built by Harry Collis in the 1910s, and throughout Flossmoor's heyday, it played as a ~115 yard hole (from where the front tees are now). Much later, in an effort to add length, the club moved the tee to where it is now, requiring a long walk out of the way and further into the woods.
That's an interesting point about the tree on 14. I typically hit a driver over the tree, and it's not in play, so I don't think about it much. For those who can't do that, the tree likely makes that tee shot very awkward and demanding. It would probably be a better hole if they removed the tree altogether. My understanding is that this tree in question that currently looks like it's in the middle of the fairway used to mark the left side of the tree line (although that was before my time and before the Hearn renovation). So Hearn opened it up quite a bit by clearing out all those trees, but he did leave that one for aesthetic/strategic purposes. However, the original tee was well to the left of where it is today, so most of those trees wouldn't have been in play.