I think this is another example of the QWERTY effect. Obviously, there are many pieces of word processing software that are superior, but he is so used to his system that, to him, the transaction cost outweighs the opportunity cost.
It seems that all he cares about is writing text, period. A typewriter is not good enough because editing is a pain, but Wordstar 4.0 seems to fit his needs perfectly. How is there anything wrong with that?
A lot of software is novelty-driven, because you need to sell your users on the next version. Sadly, this is often at odds with the goals software should aim to fulfill as a tool. Did we ever need a v2 for the hammer, or drafting pencil?
Clearly, innovation is good - the modern (1514) hammer is better than the big stone our Homo Abilis ancestors used. But at some point, you reach an upper bound.
But there are other things you can put on the other end of a hammer besides a claw, none of which made the original hammer a bad idea if all your problems really are nails that you don't need to claw back out.
Some of it is driven by available technology. It would have been very hard to have a great spell-check functionality on early home computers, like my 48k Apple II+, simply because of the hardware.
Did we ever need a v2 for the hammer, or drafting pencil?
Hammers did indeed evolve quite a bit from their stone age original form, though the general shape and principle have remained the same.
There is a modern claw hammer halfway up the left side in this illustration from 1514:
http://en.wikipedia.org/wiki/File:Melencolia_I_(Durero).jpg
Drafting pencils have been around from the late 1500s:
http://leadholder.com/main-history.html#leadholder_origins
It's arguable that truly modern ones didn't appear until the 20th century, however.
Uh, yeah, both the pencil and the hammer not only have gone through multiple iterations over history, but have a branching family tree with real improvements for specific roles over time.
Sure, there's a lot of fluff in software (and all kinds of other products), but technology actually does bring improved tools.
Well worth a read (1996): http://reason.com/archives/1996/06/01/typing-errors