I was experimenting with making a font a while ago with software that was painful to use, then recently found an illustrator plugin called fontself which is really super easy to use. Just group letters like i j together, then drag / drop the alphabet into the plugin.
If there are any easier tools out there I would love to know.
Just incase anyone else wants to make fast fonts out of calligraphy. It is always nice to have non-copywrited fonts in your collection, and this is simple to use.
I used an iPad app years ago called iFontMaker it was real quick to make hand lettered fonts. I even got my 12 year old daughter to make her own font. I would print out short stories with her handwriting to encourage her to read more.
You should engrave those for posterity and set them aside. One day you can roll them out, and remind them of their childhood, perhaps when they have children.
I named the font with their names / ages. And made this for my father. A spray painted tile, negative image burn. Though it took off a little too much. I still haven’t mastered the brightness / contrast to get this perfect.
j/k my 6y/o’s handwriting.
I have always had a love for fonts. And wav files. 
