While obviously it's possible for you to take this on, I'd share your reluctance. Frankly, our group would consider it too much risk and red tape: The issue of employee vs contractor, benefits, workers comp, performance reviews, who supervises/disciplines/rewards this person.
If we had the funds and agreed with underwriting this, we'd give the school the funds. They are already set up to adminster payroll and to understand these issues. But our PTO would not be willing to take on the role of employer.
Due to an extremely complicated situation our principal has asked our group to look into directly paying one of the school employees from our funds. In the past we have given the school the money to pay this employee and everything worked out fine. However, now the principal is asking us to pay her directly.
I know that we would have to decide to either "hire" this person as a contractor or a direct employee and we would have to start issuing 1099s or W-2s (the salary for this person is about $14,000 per year). I'm not sure this is something we are willing to do. We are a large organization and the money is not the problem, but I'm afraid the paperwork may be more than we can handle. What happens if the school pays the bulk of the money and we only pay a portion of it? Could we consider the person an consultant then? There are no benefits involved.
Has anyone out there successfully done this? Thanks for any advice on this topic.