I can't see why cutting the bottom would make it last longer. To me, I see more drawbacks to bottom cuts, compared to cutting a top lid (for the reasons GeologySage mentioned).
I think the main benefits to a bottom hole would be... it's easier to place a pumpkin over an already lit candle... and it just looks "cleaner" to have the top of your pumpkin untouched and natural.
But I'm used to jack-o-lanterns with lids. That's the tradition, and that's my preference at least.
As for lighting candles deep inside a pumpkin, those "long lighter thingies" are certainly the way to go. I have a few
Scripto multi-purpose utility lighters.
If you can find one, go with their Wind Resistant Outdoor Utility Lighter. Its "jet flame" is like a mini blow torch flame that won't blow out. This item is hot, so to speak.