Here's the deal. I'm new to machining, and new to the company I'm currently with. I've been running AutoCAD LT for years, and I've got a nice Gerber Sabre 408 router, so I'm not new to CNC, but Gerber uses their own interface, and I've never dealt with G-Code as a result...
We've got a Haas VF-2ss that hasn't been used for a few years. I'm busy cleaning that thing of dried coolant (do not let your CNC mill sit with coolant for years, trust me).
There is in fact, no CNC software here. There never was any apparently. They had someone outside the company doing their programming, and just loaded files. So I'm working from a blank slate on that side.
They do run Solidworks here. My intention is to dig in to that to get up to speed. So, by extension, I thought perhaps HSM would be a good choice to go with for toolpaths. That said, as I'm up against a steep learning curve, I don't think a 30 day trial of Works would get me up to speed. So the real question is this (can't believe you got this far...)
How close are Express, and Works? If I take the time to run with Express for a while, is that time well spent that will apply to Works? For what we're looking at currently, 2.5 axis will be fine, but I will want to go further down the road. If that means I'd have to essentially start over, then I probably should just push for what the final software choice would be. Logically, I'm sure they're close, but I've seen AutoDesk do some mind numbingly stupid things in the past...
The shop that has been making our parts runs Mastercam. I could go down that road since they have indicated they will help us (our 1 mill is no threat to the amount of parts they make for us). My understanding, however, is that Mastercam is pricey, and a steep learning curve. I'd like to minimize the hills I have to climb since I'm starting at a really low point...
-Tim