Is it reasonable to say that one day we can have fonts that are more organic? Ones where the computer knows to vary the same letters so it doesn't appear completely superficial.

I think it would be a very cool concept to start intergrating more organic things to fonts in general. I think the thing that really limits computer fonts is how perfect they are. Yes, they are very legible, but they display a cookie cutter output for each letter. This sometimes detracts from works when computer fonts are used because they are unnaturally perfect. I wonder if it is possible or even reasonable to develop a way for the computer to make slight alterations between each letter. This would give it less of a rigid feel and make it more comparative to hand-written work, which show great variety. But I do wonder what this would do to accessibility because I think it would require much more space on your computer. Overall, I think it would be a cool idea, but like many other ideas, it has its limitations.