[brudgers]

What has he been doing besides looking for a job?

If it's been writing code, building something, then yes you should hire him.

Otherwise, go with your gut - either steer clear or pay per deliverable.

[anarcticpuffin]

Unfortunately it may be latter. I think the combo of your idea and staunch's may work. I'll give him a pay-per-deliverable quick project as a trial run and see if he just needs structure to get into it. If not, it was a gift of some money in a rough patch.