I know your pain!! I'm a teacher too and suffered the transition from XP to win7 and now win10 (Makes me want to cry at times!!)
Techsoft is pretty straight forward to pick up/use and can be configured in simpler modes removing the more in depth features. If you go to their web site you can Dload a trail version you just can't save or output from it.
You can set the size of the design page to meet the material or bed size. draw in different colours, lines, shapes, you could say draw a rectangle with the rectangle tool, then radius the corners using another tool setting the diameter and then clicking on each line into the corner.
Text can be placed in a box, on a path or just free in space. once placed it can be resized in the same way you resize a picture in Word. (you can do that with anything you select on the screen). You can use out line fonts (normal text is an outline that is filled in) or single line fonts (great for engraving with a V cutter).
Now in the early version of 2d design you could set depths to colours but as you have to export as a DXf in the new one I'm not sure if you can do it like that. You may need to just select the different paths in VR5 and set the machine depths in there. If I get chance I will have a look.
I use 2D design with Y7-11 with progressively harder projects. I start out with outline of a steady hand game base, they have to add the text, locate the position for the holes for the LED, reset Switch and wire shape (so they get used to using measurements on the screen. Extension material is to add some form of drawings, where they have the chance to 'play' (get them to draw large and then reduce). These are then laser cut from acrylic. By the time they get to Y11 they can design 5th scale models and laser them out of card and develop them for GCSE before full scale production.
I used to do a lot of 3D milling with the Micromill, half bottles for new drinks, aftershave etc in modelling foam and do point of sale displays.
Other projects have been engraving door signs in Pine or acrylic. You can get laminated (2 different colours) plastic which when machined with a V cutter or ball nose gives a good effect.
The other option would be to get the It guys to sort out an old PC with XP and all the old software on. It would be better to move forward though. What CAD programs do you have? all you need is something that can export/save as DXF for VR5 to import.
Just a note, I'm nothing at all to do with techsoft, just I have used it since 1996. http://www.techsoft.co.uk/Products/Software/2DDesignV2