An interesting topic.
I looked over Windows vs OSX programs
Windows MovieMaker vs iMovie
Windows Premier vs FinalCut
And I use Sony Vegas and Camtasia semiregular, as an amatuer, nothing professional.
The things I wrestled with were first the "Linear Editor" versus "Storyboard or Clips" approach to editing.
The "pros" use linear editors, the "amateurs" usually use storyboarding.. basically because the "pros" like to go back and forth switching and swapping clips.. and the amateurs just want to point and shoot and never look back.
The "defining" difference between a Linear Editor and a Storyboard is layers or "tracks". A storyboard essential has one track for everything, video, sound, title, end credits.. its one single "thing" and very straight forward for amateurs to think about. A linear editor has many tracks, which can be sequenced and brought in or out, faded in or out, or rearranged and blended together like the elements in a multi-level drawing or photograph. Keeping track of all those possible elements can be confusing and time consuming for an amateur and complete over kill for their purpose. I've heard some people say Linear Editing is like "Painting with your mind" and the "Final Cut" is only one possible rendition.. which is why Linear Editors always "Save as a project" and have to be purposefully told to "Publish or Render" a movie.
Vegas is very much a Linear Editor.. it demands setup, and finishing touches be explicitly done by the human editing.
Camtasia "used to be" firmly a storyboard program, which teachers and coaches loved.. but they changed focus and have been trying to become a Linear editor since version 8.. which has confused their user population a lot. Perhaps for this reason.. they are perfectly okay with owners of version 8 downgrading to using version 7.. as long as they remain customers.
Premiere and FinalCut are also very much linear editors, and there is a fascinating Wikipedia article on the origins of Linear Editing.. basically it comes from the VHS or Video Tape era which was made to mimick the old Cellulose Film approach.
MovieMaker came from PhotoStory and took the Storyboard approach, pick a few clips and let the program string them together and bookend with a title and closing credit and done.. very little human intervention required.
iMovie was somewhat like MovieMaker, and the later iOS version
I guess its only fair to also mention Apple dumbed down FinalCut in version 10 (or 'X') to be more storyboard "like" which is really odd since Camtasia seemed to be going in the other direction. Apple is a confusing company. The hardware keeps escalating in quality, the software keeps regressing.. together I guess they balance out.. but I never expect a lot of predictability from Apple products.. just a premium price.
Integration between Adobe programs came about mostly like Windows Office in that they strung them together with a metalanguage that allowed an extended workflow between the programs. PhotoShop was especially good at color correction.. and could render.. but took a long time. Aftereffects was good at tweening.. Illustrator was also good at vector graphics, which are great when your trying to do overlays to fit on top of a pixelated background where the resolution can change, with vector graphics you don't have to redo your artwork.
Dividing up the workload between programs that specialized in one feature or another.. is not unlike the Office Suites of old.. Lotus, Microsoft, Wordperfect, Corel.. ect.. you gather a cluster of programs and sell them as an ensemble.. or as Adobe has done.. rent it with promises of upgrades.
The key to Microsofts success was arguably their "hard disk is a file" with OLE2. Office documents became proprietary "virtual hard disks" such that .doc files could contain a seperate file for every kind of program in the Office suite arsenal. But the .doc file was a compound document, which most competitors didn't understand. This was around the time pkzip and Arc files and Tarballs were coming into use.. but no one else seized upon it to support "workflows". Creating a virtual name space.. simplified everything for users and every Office document became a "project".
I will be the first to admit its overwhelming.. but what I have done is try to focus on those tools I already know or am best at using.. and nibbling on the more advanced ones if a need arises. In the meantime.. studying their history on Wikipedia helps to put them into perspective.. so I don't waste too much time trying to use the best tool in every case.
The best tool is the one you already know how to use.