I have not been cutting for that long and have to cut alone most of the time since my son was born last year... both have kept me very careful. The farmer always knows where I am cutting and he comes up or sends someone up to checks on me if he has not heard the saw running in a while.
But... last year I was dropping trees the night before woodcutting on the farm I hunt. (woodcutting on the farm is when all the hunters cut 10-15 cord on the 2nd Saturday in October for the farmer to heat his house.) I had a big half-dead cherry I was dropping about 20ft into the woods from the field. The tree was 30+" at the stump and stood straight up with no lean but had extra foliage/branches on the field side and there was no wind. Thought it would be an easy one. First mistake! Notched it (but not too deep as a lot of the cherry around here is rotten in the middle when it gets any size to it), bore cut, wedged it, then cut the holding wood... I should have known things were about to go wrong when I had to cut the whole strap for it to go over. It was just starting to go as I finished cutting through the holding wood. The gap open a little as she leaned and I pulled the saw and booked it out of there... as all of this was happening the wind picked up and pushed it back on the the wedges... oh wait... the crappy short wedges I had fell out when the tree started to lean!!!
Tried to pound the wedges back in... no luck. (lesson learned 6" wedges are almost useless... I carry 12" wedges now, the extra $2 per wedge is well worth it!)
I drove down to the barn to talk to the farmer and get extra chains to pull it over. Farmer told me to leave it overnight the wind was supposed to change direction and should push it over during the night. So on his advice (not doing this again) I left it to fall overnight.
The next morning I arrived extra early, it was still standing and the wind was pushing it toward the field.
I drove back down and told the farmer to warn everyone to stay 100' away from the tree line when they drove up on top of the ridge because we were going to have to pull a tree over that was refusing to fall. (this is pretty normal at the farm, until I did one 3 years ago none of the guys that cut on the farm had ever seen the bore cut method of directional falling, this has made me the official feller for the group and earned me the very aggravating nick name that first year, thankfully it did not stick )
As the other guys were starting to arrive I had to tell at least 2 of them to park buy my truck since they drove up and parked under the tree even though they were warned to stay away from the field edge!!!
I had just gotten enough chain together too have a little over 1 1/2 the trees height in chain and was starting to walk toward the tree with the first bit of chain when the tree came down. If it would have come down 5 minutes earlier the trunk would have crushed one truck for sure and the limbs would have done some damage to another, I try not to think about what would have happened to the guys who were starting to get there gear ready at each of the trucks.
Needless to say it was a learning experience for me, I now have appropriate length wedges and 120" of heavy tow strap and chain in the truck any time I go out.
Aaron