It is my feeling that Version 3 is archaic by today's standards in software design. Workstation 4 is a much more feature rich and flexible platform. The tutorials cover the basics pretty well and from my experience with the hands-on training of many people is fairly easy to learn. Huntron has also been adding support of test instruments other than Trackers for the past couple of years. As far as I know, there is not a software package out there that does what Workstation does as far as creating guided test procedures and providing comparison capabilities to stored test measurements.
As far as cost, software development is an expensive proposition and as a company Huntron needs to recover the cost as well as keeping the product moving forward. The test equipment industry is a niche that does not see the volumes of consumer related electronics and software so it will be inherently more expensive.