Ok, I think I got it. I utilized a one to many for Contact to Work Orders. I set up some conditional drop down and it works. The one thing is that I only tried it for one contact, meaning I only have one contact field in the form. If I do it this way, then there are going to be a total of 9 fields: contact Type (drop down menu), contact name (drop down menu), Contact phone (auto-populates).
There has got to be a better way to do this, where the 1st field is always and only for contact types of: Site Supervisor; the second field is always and only for contact type of: job contact; and the third field is always and only for contact type of: home owner. Granted, each of those will have an associated telephone, but at least that would knock it down from 9 to 6 fields.
Any thoughts?