I've never had to prepare one as we always took the easy way out and ran it through the school. If our PTO agreed to cover a special performer or program where an individual had to be paid (more than $600 where a 1099 was due), we let the school arrange it and the PTO granted the funds to the school. This was a common transaction for the school district, so much easier for THEM to handle, although I don't believe it's too hard.
We do have a few active members on the Forum who have issued these. Here's a thread from last year that might help you.
One other note - you have to be super careful that what you are doing is purchasing the services of an independent contractor that qualifies for 1099 and not work that could be considered employment. That can be a very tricky area. There was a discussion on that a few months ago if you do a search.
Our bylaws specifically state that we are not allowed to pay anyone for services or time spent on PTO related activities. But I would think you need to provide a 1099 so you can track the money you are paying to whom. Also, it will have to be recorded and filed on your 501C3 application since it has an impact on how they view your organization.
Do any PTOs on this site currently issue 1099s for individuals who run short term (one shot deal) programs after school? It would be helpful to our group if you could give us a run through on the process.
In addition, in the future we hope to receive grant money (once we become an incorporated 501C3) to run assorted programs. How does this process work?
Thanks. As always, I am trying to get some initial education on these topics and this site has been helpful!