Yes. Just like the T3, skippa will record all back-to-back recordings on the same channel with your pre-set padding included, even if the padding overlaps another recording on the same channel.
I am not familiar with T3, so can you explain further please? If it includes padding on both, does that mean that two back-to-back recordings will use two tuners? The only system I am familiar with is the way TED handles them - that is merging the two, on one tuner. Hence you certainly wouldn't miss the end of one or the beginning of the next, but can easily separate the two afterwards if you choose.
The way Media Centre does it, it does include separate padding on both shows, using both tuners, hence it is impossible to record another show on another channel (as I have dual tuners there) - not my preference
The T3 only uses one tuner to do this. You will end up with each show in its own file with pre and post padding all without needing to use a second tuner.