Great questions Mike. Here's my take:
1. Each guest needs to call into a separate skype account.
2. Wirecast allows a "Virtual Camera Output" essentially allowing you to easily share the program output to a Skype caller
BUT it does not work when you have skype running on a seperate machine (which is actually the correct way to do this) Sending a program output feed to the Skype callers is not incredibly hard to do, but connivence, price, and quality all go hand in hand. For the cleanest return video, easiest thing to do would be to take for example the HDMI output of your Wirecast rig, send it through an HDMI splitter, and then run the split connections to their own separate inputs on each machine's HDMI capture card. I use an AverTV which works decent for the price, but you could also use a Black Magic Intensity Pro. If you want to save some $, a few years ago I showed off a much cheaper way to do skype return video. Quality isn't nearly as good, but if you just want to give each guest a live feed so they can see what's up on screen, this will work. I detailed my
setup here, and feel free to ask any questions if you have any.
On a sidetone, if you go with Mac Minis, PCI cards won't work. You would want to go with the Black Magic Intensity Shuttle Thunderbolt Edition
3. Desktop Presenter will work, but certainly not ideal. It's always good to try it before buying any extra equipment , but I've always run into frame rare issues and it will never be as smooth as capturing the actual output into a capture card. Again, you'd want to go with either the AverTV or BMI Pro, and put 2 of these into your Wirecast rig. Take the HDMI output of your Mac Minis and feed them into the capture cards. If budget allows, there's nothing wrong with Mac Minis, but PCs usually work just fine as Skype Machines and offer more flexibility and capture card support.