The newer boosters have self levelling legs which remove the lean caused by uneven crushing of the landing leg cores.
Sure enough, one of my friends I went with landed with his legs apart, despite the instructor yelling at him from the ground. He shattered the leg he landed on. (Parachutes weren't as gentle in those days.)
I expect it would be the same problem with the rocket. Any movement sideways when landing means the force is going to be on one leg. I wonder how they deal with that.
There's footage online of some of the early landings when the robot had not been implemented, where boosters slid across the barge in part due to landing at a bad angle.
So it seems like they expected the risk of loss of the booster to be low, it just so happened that this time things went wrong.
They have previously delayed launches due to poor weather at the barge. So if that was the case this time, they would've just postponed, unless I guess they weren't really worried about losing a life leader booster that was apparently too old to be worth retrofitting with autoleveling legs.
Isn't it crazy that almost all of their competitors dump the whole first stage in the ocean every launch?
If you need to optimize for both the launch weather and the landing site weather, your launch windows are even more limited. At the end of the day, losing an occassional booster isn't a reputational problem; losing the payload would be.