I almost took a job a few years ago that used powermill. I've heard a lot of good things about it, and know a few shop that use it. The job was terrible though, and the only good thing about it was the opportunity to get away from edgecam lol. From what I've heard powermill is huge in your neck of the woods. With WorkNC being popular in the fixture shops down there.
I've heard good things about WorkNc too. We will be looking to upgrade here this year sometime, and I want to evaluate a few different packages. We do a lot of 3d surfacing, so re machining strategies are a big factor for me. Edgecam sucks in that department. Great if you like cutting air, and rapiding all over the place picking out phantom remnants of material the software thinks are there. I found a couple good workarounds over the years to mitigate that, but it still sucks. The latest version we have is 2014, but seeing how little it changed from our 2006 seat I don't have any hope that a current version would do better.
I've always equated CAD/CAM to driving a car. I've always been pretty quick to pick up new software, and find all the workarounds to get it to do what I want (they all have them). When you learn to drive, you don't learn to drive a Buick century specifically (for example). You learn to drive a car. You can then transfer that experience to different cars, trucks, vans etc, where the knobs and buttons may be in different places. Some have more options than others, same with power, and performance, but they will all get you from A-B. If you have experience driving, you can figure out how to drive new vehicles pretty quickly. CAD/CAM is the same way to me. Learn the fundamentals and how to apply them to build a solid foundation of competence, and you can hop from software to software with a relatively quick learning period because you know what you're looking for. They all have strengths and weaknesses for the work you do, and with such a wide variety of work, and workflows out there, there really is no one size fits all solution. Though NX is pretty nice I've heard. I haven't used it since it was called Unigraphics back in college.
Good idea about the student rate. I'm looking to take a PLC programming course this year, and will look into the student eval copies of software available to me.
Cimatron was hit or miss for me. I worked at a shop that used it about 16 years ago, and I was forced to use an older version for designing. I absolutely hated it at the time, but managed to get by. Apparently the newer version of it was MUCH better, a complete redesign, but at the time, they weren't buying another seat for me, although the 2 guys on either side had it. Fast forward a few years working at a different shop we hired a contract guy that used it. I got to play around with it a bit, and found it much different than my previous experience, I found it pretty powerful though still a bit quirky, more seat time would have been better. It was great for mold work though, which is what this guy did primarily.