I don't believe you need to be more experienced to jump a stowless bag. It's just different to pack, not more difficult. Just ask someone competent to show you how to use it. PD doesn't recommend any of the semi stowless bags, because they believe they are not all created equal and some don't have enough tension on the lines for a good deployment. I've been jumping one for about 175 jumps and prefer them to normal bags.
Charles Lindbergh bailed out successfully 4 times, 2 at night. I remember seeing a video from a jump plane in an inverted flat spin from wich the pilot bailed out at the last minute, but I don't think it was in the US. just found it: http://www.liveleak.com/view?i=3a9_1345519037&comments=1