Hello my friend, I hope you are well!
I have developed an auto Skype responder many years ago for an old client of mine, along with yahoo and windows messenger bots in the past. With over 8 years experience specializing in developing automated bots I can say I am an expert when it comes to this subject. I can develop you an automated Skype bot that auto responds to messages, and the rest of your requirements within two days. The desktop application could only be run on a windows computer as I develop in .NET. I am an honest developer and I can say with confidence that my solution would be far greater than the majority of the freelancers here. I have a superb feedback and history here, so please check it out too.
I hope to hear from you soon, sir!