Trail Files...potential or dead?

They are a mixed bag. The low barrier is attractive, but the lack of error handling and generalization means they are tough to apply. Make even a minor change to a model, or as you mention, move a window, and the trail file fails.

They are recorded the same as mapkeys are, which suffer the same problems. I think they really represent the internal calls to software and aren't designed or intended to be human readable; possibly the opposite.

I've taken to externalizing control using AutoIt, which is much more flexible and easier to move across versions of software. If an operation fails, I can create an alternate action to proceed, unlike trail files which simply quit. I do use mapkeys from AutoIt to run difficult to monitor sections rather than recording detailed mouse and keyboard actions, but the control is all on the AutoIt side. (I presume the experience of AutoHotKey users is similar and that VBA from Excel or Word can also perform the control function.)

It's hard to tell.

Generally, people tend to avoid tools that aren't documented well enough. That's one of the reasons i favor Autohotkey.

Take this example of trail file setup: 2014 PTC LiveGlobal Mapkeys TrailFiles Presentation Video - YouTube

I guess the presenter had to go long ways, and dig pretty deep to figure this out,

This are some very interesting points. Yes, Error handling and documentation would be very helpful!

Both of you have mentioned using alternative programs to automate rather than using Creo's trail files and mapkeys. I have heard of both AutoIt and AutoHotKey, however when I discussed with our IT department to see if I could get one of them, they leaned heavily towards Powershell. Are you familiar with it and how well it works with Creo as compared to AutoIt or AutoHotKey?

Thanks!