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Free drawing software; how to choose the best programs
This applies more in some fields than others, CAD for example. The reason I would recommend DraftSight for 2D CAD work is its similarity in command structure to AutoCAD, which is the industry standard, and by implication therefore, to other CAD software like the IntelliCAD group. It means that you can open DWG files ( The CAD standard file) easily. It also means that your skills are transferable to other software.
This may be more important from the point of view of teaching a program, as you want it to have the widest appeal possible. However, imagine you have spent months and even years developing skills in a 3D drawing program like SketchUp using a PC, and you are planning to buy yourself a nice new Mac next month; no problem, it runs on PC and Mac, but what if it didn't? Viable software has to be truly cross platform.
This is a tricky one, and sometimes difficult to judge, as there are 2 types of well supported software; community based and corporation based. Blender, for example, is a cross platform open source 3D program with great community support; SketchUp has established itself in no more than a decade as a global presence in the 3D design world simply because it was owned by Google. Of course it is also free, very user friendly and has great online learning materials. Unless a program has the backing of either a very active community or a major company, its unlikely to stay the course over a number of years, and even less likely to be truly cross-platform.
Maybe this should be top of the list, but there are many many free and excellent programs to draw with out there, so its important to start applying other filters straight away. The great thing about free software, apart from not having to pay for it, is it tends not to suffer from "bloat", or the constant addition of unnecessary features, added by the publisher to try and get you to buy the latest upgrade. Its really incredible the number of great commercial programs that have been ruined in this way.
Well, again, maybe this should be further up the list, but honestly, before I'll even look at a program to determine whether this applies, I'll go through most of the checklist above. There is no point in spending time testing software unless it meets the other criteria here.
Free software has come a very long way since the early days, and its moved more and more into the mainstream. There are still many great programs out there supported by a small community of dedicated enthusiasts, with a relatively small user base, that do a great job. Some of these programs are undoubtedly worth a look, but like everything else, its a numbers game, and its hard to keep up with the speed of change in the computer world if you don't have the support of a large community of developers and/or users.