hmm.
i don't think you're going to be able to accomplish this with dynamic components..
i'm not quite sure how the jumpers are supposed to look when filling the awkward shaped roofs but i assume they will be cut on angles.(?)
basically, if you can't use standard sketchup's Scale,Move, & Rotate ( , , ) tools to modify the components then you can't do it with DCs..
(there are workarounds such as shown in this stair building dc of mine.. i made the video to show the suTeam some requests of mine but you'll probably be able to see the limitations you're up against here:
http://www.youtube.com/watch?v=2QYs1lcrAck )
so, try taking one of your jumper components and using only the tools i mentioned earlier, conform it to your desired shape.. is it possible?
also, with DCs, you can't just click on one of the odd surfaces then have the components populate the area automagically.. you'd have to enter all the parameters manually via a component dialog which would be easy enough to do with the rectangle shape but once you get into the varying angles/cuts/etc, you're going to hit a dead end..
this would be more suited to ruby and there are people on these forums that could (probably) make a plugin for you but, it's so specialized of a plugin that i don't think they're just going to make it and publish here as nobody but you needs it.. it seems like a situation for contracting one of the writers to build the plugin specifically suited to your needs.. if this is for your business, i'd say it's a route you may want to explore as it's going to save you tons of time over drawing these things manually per each roof.. i don't know how much they'd charge to do something like this but if it were me, i'd be expecting something in the $100-$500 range(?)