As someone who’s been in this field for quite a while now, my experience in working with most freelance bookkeepers is that...they’re terrible. It’s a trade that has its fair share of thorniness, and most freelancers I’ve worked with simply don’t have a sufficient grasp of it (or are simply unmotivated to care enough to follow through).

With sufficient (very deep) automation it can be done properly, which is what Pilot seems to be aiming for.