I think I have the multi-dimensional sorting piece figured out (just sorting by start times) with:

@combined = sort {$a->[0] <=> $b->[0]} (@listone,@listtwo);
[download]

What I really need help with is the piece that covers those two difficulties I mentioned in the original post. Something like:

@combined = sort {$a->[0] <=> $b->[0]} (@listone,@listtwo);
foreach (@combined) {
     #check for overlapping times and make sure the smallest V time is
+ listed during the overlap
     #XXXXXXX

     #break the timespans apart if it covers the crossing of a new day
     #XXXXXXX

}
[download]