Skype on Linux isn't as bad as many think it is...I guess. At least for me the most important features work as good as so I would never come to the idea that I needed to boot windows in order to have a convenient conversation.
There are some minor "flaws" though - e.g features in the UI microsoft didn't (want to?) make work on linux. One of those is the fact that you cannot simply drag a file from nautilus/konqueror/thunar (I only confirmed thunar, so correct me if this is an xfce-only problem) and drop it onto the skype window to send it. Thus, you will probably need to click on the (+), then "send file" and the navigate to the file (again). If you are used to have the system file manager open in the file-to-send's folder next to your skype window, this is not really a nice workflow to be honest, compared to what is possible in the windows version.
I spend quite some time researching on this, so I guess that I have to tell that this lack isn't "fixable" as of now unfortunately (although I would be glad to have someone correct me here, too).
BUT I just found out another way to simplify the process by accident:
Skype seems to accept files to send from the clipboard!
I hope this text will be findable in google so others may see this alternate solution, too. If you like this "workaround" or have a better solution, leave a comment.
Until then: Good bye!
Yours suluke