Randomize Altertenates

#1

I have created a handwriting font with (approx 5) alternates for each letter.
I would like them to randomly change while I type? Suggestions?
I used the illustrator plugin to create the handwriting font and I believe the author is typesetting in Photohsop but thats negotiable

#2

I don’t think that’s possible in Fontself. You should be familiar with OpenType programming and access to FontLab or Glyphs.
maybe these will help:
https://glyphsapp.com/learn/features-part-3-advanced-contextual-alternates