Hello Mark,
Eons ago when I took CS classes I was told to spend 80% of the time planning and defining a problem and 20% of ones time codimg.
Programmes--- check out the Elance site. If the programmer does not perform to your complete satisfaction you do not have to pay. So it is the programmers responsibility to do a good job. The unsatisfactory programmers soon get weeded out.
Video's-- Seems that you are making a big production of what is now a very simple process. All you need is a mike ( input ) and speakers. Download Jing it's free and gives you 5 minites of video ( screen capture ) per video. Start your program, then use Jing to record your voice ( explanation ) and screen movement. Very simple really. Does this site allow attachments ? At first glance this site seems rather limited in it's capabilities.
Software-- being tied to a point gives rise to many scary and unsettling possibilities especially after one is deeply into using it. There has got to be a better way. Licencing is totally a valid concern and so is payment but then one should be free to use it without worring about servers, incapacity etc.