I currently have Skype working within my solution, where it will dial out, pause for 15 seconds, then using the speak script step, will speak one of three different messages based on field content.

Is there any way to have the 'system' or FMPro only speak when the call is picked up on the other end (instead of the random pause script step)?

I think I would hate your solution   I don't appreciate being talked to by a robot...

Having said that: check out the Skype API, you may have create your own bit of middle-ware to do it.  If Skype has a java API for instance you can see if you can write Groovy code and execute it through the 360works ScriptMaster plugin...

I think I would hate your solution   I don't appreciate being talked to by a robot...

+ 1

and then waiting for the other party to answer. I just hang up, but not before I banning the number it came from.

You may wish to check out DialMyCalls.com its a IVR Voice Broadcast Service with affordable rates for calling, that provides you much more robust features such as, being able to determine human or answering system. https://www.dialmycalls.com

You can actually record a message in a human voice or if you prefer use the text to speech "robo" calls. 

uses standard API's that you can use BaseElements Plugin with. 

I did some integration a while back. http://fmforums.com/files/file/61-dialmycalls/

Thanks All - I would hate my solution also. Just to clear my 'good name' - This is a student-based solution to checkout equipment. When they are late returning equipment, I want to hound them automatically. Students also run the checkout room and would be the users of the solution.

I currently have Skype working within my solution, where it will dial out, pause for 15 seconds, then using the speak script step, will speak one of three different messages based on field content.

That reminds me of a voicemail message I had at one point on my mobile. The voicemail would start with "Hello", then wait for 3 or 4 secs, just enough for the other end to say their name, then my voicemail would go "Hey! How are you!", at which point the other end would start talking, and my voicemail would wait 5 or 10 secs, and then continue "Unfortunately I'm not able to take your call... yada yada".

People kept falling for it.