I had zero issue with working alone residentially. But I never asked employees to do it.
This.
Mostly, when I've been climbing, I've had an experienced, old, slow climber, or guys that I wouldn't trust to slap on gear and get themselves safely up the way.
Deva, how is your safety record, situational awareness, ability to stop when you should, etc?
Have an emergency contact list, family and other tree climbers who you know who will come bail your ass out in the event the fire dept/ rescue can't, which is most times, around here. A city might have more of a bucket/ ladder truck access. Planning for the contingencies helps you avoid them.
Working alone as a lone cowboy is one thing, working and climbing alone when you're a husband/ partner and parent is another. You should be a lot less likely to make any "aw F-it" choices.
When you're working alone, and doing clean-up, it doesn't matter is you're a superstar climber and pruner/ killer, you're doing grunt work. Decide how much is sensible and how much to have an employee. Consider an employment service for occasional grunt work.
Working alone, you have no distractions of supervising employees.