Funny you should ask something like that...
I've been working on two projects the fast few weeks, both related to the fact that I have just started running my first Traveller game since the late-80s that are related to what you asked.
The first is a MS Word-based character sheet for MgT. I started with a simple form, then added some drop down boxes for the skills, and careers. Even linked the career-branch selection so if you pick say "Rogue" it will only show you the specialties for the Rogue career. Then I added logic to calculate the ability modifiers (have a Dex of 12, get +2, etc) and even range modifiers for ranged weapons. Unfortunately taking it any further than that would have required me to start over completely and re-write everything in VisualBasic and I just didn't see the value in that. But it still is a pretty cool form, and I can convert it to a PDF, but it will loose the automation parts.
The second was something I mentioend in another thread. Taking the JavaScript-based Megatraveller Character Creation tool hosted
here and using it as a base to create one for MgT. The fun part is that when I started this project (on Presidents Day) I didn't know any JavaScript. Turns out the MgT process is probably a bit to complicated and involved to do this in JS, but I am slugging away at it and learning. I've got it to the point where it generates the UPP, creates a homeworld, and takes you through the first term of a career (without events and mishaps). But then it goes boom. Still working on understanding how JS works when it comes to controlling the flow of an application.
I didn't know that you could use JS to automate a PDF form though. That provides a *very* interesting idea for the next step of the character generator app. I was wondering how I could then get the info into a nice format to print, and that would be the answer.
Of course I would have to get to that point where the application is complete and that is a big if. There is way to much data for me to type in as JS variables, objects, and arrays to do the complete process for MgT. Though I guess for other versions of Traveller (like CT or MgT) it might be easier. I've tried creating characters for T5 by hand and still aren't sure I've gotten it right, so I won't even go there with the thought of automating it.