How awesome he is teaching himself cursive! We are homeschooling this year so I am teaching my younger two cursive as well. I am making it up as I go along but Michael Sull has a wonderful course.
http://www.spencerian.com/americancursivepromotion.htmlI think you can order it through John Neal and Paper & Ink Arts as well but the link above goes into more detail.
I think it is important for them to master the basics before they move on to pointed pen. There is a frustration factor involved with getting the pen to even work, let alone making the correct letter forms. However, I have introduced all of my kids to a pointed pen around age 7 just to get a feel for it. They were thrilled when they could write words with it but I think they are a long way off from actually doing cursive with it. However, every child is different! My kids have handwriting issues anyway (go figure) and low muscle tone so it is a bit of a challenge to manipulate.
No harm in giving it a try!
In terms of other lessons, people really like handwriting without tears but I don't care for their letter forms. I have created a manuscript lesson for learning print. I will post it at some point, but it isn't cursive. This is another great resource
http://www.handwritingforkids.com/handwrite/cursive/texts/index.htm but again, not crazy about some of the letter forms (however, of course, I have my own idea of what they should look like).
This is my favorite:
http://www.confessionsofahomeschooler.com/blog/2012/10/a-z-cursive-handwriting-worksheets.html. She has a bunch of free downloads, too.
