Good news: Yes I can very easily add more skypers to a chat

Bad news: At 11:30 GMT I expect to be somewhere between DC and Philly. I might even stay in DC that night because there's a concert in Farfax that I'm interested in attending.
My plan is to drive from Atlanta to Philadelphia (820 mi) that day leaving Atlanta at 5:30 am (lt). In theory that means that I'm back home in enough time to make the sound check, but I plan on visiting Megan in DC, and I don't know how "up-to-it" I'll be after 12 hours of driving.

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Here is the procedure for adding more skypers:

Needed: Two computers, 2 (long) AC standard mono audio cables (for use with computers), possibly 2 audio cable split depending on the computer, two skype accounts

Designations: As shown above two of everything is needed. These components will be split into groups "A" and "B".
line out: aka speaker, headphones jacks. These are usually a green colour, sometimes black
line in: aka line in jacks These are usually a blue colour.
mic: a kind of line in, specific to microphones, using this jack is very undesirable for this application, usually pink colour.

Procedure:
1) Run an audio cable from the "line out" of "computer A" to the "line in" of "computer "B"
2) Run the audio cable from the "line out: of computer B" to the "line in" of "computer A"
3a) "Computer A" should have two "line outs", a regular line out and a speaker line out. If not, use a audio cable split to connect the speaker for the syper present at the computer to hear the conversation, and another cable to the "line in" of "computer B"
3b) "Computer A" should also have a line in and a mic line. If not use a audio cable split to connect the microphone and cable from the "line out" of "computer B"
4) "Computer A", using "Skype account A" will re requested by Sadgeezer to join the main conference call.
5) "Computer B" using dummy "skype account B" will start it's own chat conference call for the extra skypers.
6) sounds checks will have to be completed to ensure proper volume. The volume controls on computers A and B will have to adjust the line in/out volumes where the AV cables are plugged in to during these soundchecks.

I recommend someone who knows how to play with wires and tweak sound controls do this procedure.
IFF someone in Preston will preform this procedure, I recommend using two laptops and you should ommit step 4 as SadGeezer (account) will already be connected to the main conference call.

This sounds a lot more complicated than it really is. I can and have set up this system myself in about 45 seconds. This is not the ghetto-rigged (jury-rigged, MacGyvered) solution. This is as simple as it gets.

Another option entails using a partitioned hard drive, and is far far more complicated, but only requires one computer. It might be possible to do it without a partition, but I haven't tried it yet

SadCAST 4 info:
As stated above, I will be unable or unwilling to be near a computer Friday. With that said I will be preparing MP3's or wav's of me giving mews items. Each item will be about 1 or two short sentences. I will have several takes of me reading each item with different emotions, within each audio file. I hope this will aid in splicing it into the SadCast without too much disruption of mood/flow.
I will have an mp3/wav of me saying "Dune". I suspect this will be used as a sound effect in many sadcasts, or who knows. Yes there will be a Dune news story.

On Thursday I am defending my master's thesis. It came in at a "lite" 141 pages. I'm going to go ahead and say I passed my defence. I'm also going to say that I and many other people in my program (and friends) will be totally pissed drunk for the after-defence party I'm throwing. Depending on how you want to edit me in, you could use this as an excuse for my pre-recorded lines.

My head hurts :)

Ok, but we probably don't need it if you can't be there.