- the keypad within the Skype client produces DMTF which can control/respond to Asterisk
- calls via SkypeIn do not
- voice applications running on Unbuntu-based VMs tend to steadily degrade over time (but probably can be fixed)
- the personal version of Chan_Skype is designed so that it only works with one license per machine (i.e., if you want multiple channels, you have to buy the business license which costs 5x more per channel)
- the Chan_Skype people need to work on their versions (currently limited to outdated versions of Ubuntu and Fedora)
In short, I like the product but really hate its shortcomings.