Text-to-speech crashes at the same point in a document when trying to create an audio file

Question

I like to convert text to audio (large documents), and have been doing this using a 3rd party app for a long time now.  The app sometimes crashes at a specific point in a text (i.e. it always crashes at the same point no matter where I start from).  The TTS also has, at times crashed even if I am just using hot keys to read a segment outloud.  At times, this live-use crash prevents me from using tts until I reset my computer.  Just recently realized I can use an automator action to convert a text to audio without using a 3rd party app.  The automator action also crashes and, after it does so, automator app won't open again without reseting my computer.

Answer 1

By the way, I have only had my shuffle for 3 months
and it is doing this. Are problems this soon normal
or did I get a dud?
I have only had a Shuffle for one week. I returned the first one to the store after a few days and they gave me another which appears to do exactly the same thing. My hunch is that it is not time-related; indeed, I cannot think of anything in the Shuffle that would change over time in this way, as it has nothing to "wear out" per se (except switches and a battery).
I do not hear any pops on mine - it just stops neatly at the end of a random song. Yesterday it went a very long time (about 4 hours) before this happened.
Mu hunch is that it is tied to the "randomizing" function within the Shuffle. When you use a playlist in random mode, every iPod effectively creates an "on the fly" randomized list. Perhaps the Shuffle goofs this up and places some gibberish in the list. This makes sense as the issue appears to be non-existent in the "non-random" mode.
I will try a few more tricks, such as different USB ports and perhaps rebuilding my Library. Seems a pain in the rear for stuff that otherwise works fine!