I use skirts a lot, because they save filament compared to rafts. I recently had a model that required 130 rows of skirt just to reach the supports at the outer limits that I was printing. It would be extremely convenient to have an option that would enable skirts to include any supports that were added. I could print only 5 layers of skirts, and know that they included the supports.
A skirt that goes around the outside of the supports isn't going to help much. I think the main problem is that the supports are pretty sparse compared to the main model, so they have a tougher time adhering the bed. So a better solution is to print the entire first layer of the support completely solid. That way you get a nice big surface area to bond to the bed, and then all remaining supports are built on top of that.
Thankfully, that's already really easy to do with the current version. Just setup a separate process for the first layer. There's several posts on the forum about how to do it.
In version 4.0, several options have been added to meet this request. The skirt now includes the support structures, so the skirt will go around the outside of the supports by default. In addition, we have added a new option to specify the number of Support Base Layers, which will add solid layers at the very bottom of your support structures. So with this simple option, you can create a solid layer at the bottom of your supports without needing to mess with the skirt at all. This setting can be found by clicking "Edit Process Settings", going to the Supports tab, and changing the Support Base Layer setting.