Yes, it does matter. The glitch only works well on the original version for PS2. On other versions the glitch either won't work, or doesn't work well and causes more problems than it's worth (PC and Xbox).
A Shamal or AT-400 will probably be the better choice because they are faster than other craft and can often fly long distances with minimal user input. It's not really autopilot, but they will fly straight and level until a storm or something sends them into a dive. The AT-400 is a bit more stable, but it's difficult to spawn - try approaching from the south using that little jump that slams a bike into the back of the hangar. A helicopter will work though, and so will a boat or even swimming.
As I understand it (I've run a lot of tests on this but haven't tried to glitch them all on PS2), flying to the southwest (and maybe later to the southeast) is generally the preferred strategy. Flying north isn't usually as productive as flying south. Traveling directly south will glitch each gang in sequence within the same zone. A diagonal path should increase the chances of crossing new sectors that glitch Ballas, Grove, or Vagos, and you'll also cut across the corners of the sectors - so you should glitch twice as many sectors along a slightly longer path.
The "sectors" I'm describing are the same size as the map fog sectors that hide the map early in the game. They make a 10 by 10 grid across a 3000m2 map, so 600 meter square sectors. You are exploiting a routing that is trying to write an 01 to an array in zone memory that will mark that sector as explored and no longer hidden. Except when you are off the normal map the math gets messed up and the game adds a single gang density instead. It all seems very random but it's not; if you could follow the exact same path then you'd glitch the same turfs.
So don't follow the same route when repeating the glitch. What I've read is that players will fly out to sea for an hour or more (real life hours) and glitch a lot of new turfs, but not all of them. Repeated attempts become less productive until no more turfs can be glitched. but sometimes it takes a while to finally find those last few zones. You won't be able to cover the whole map with this glitch. Only 120 or so new turfs can be added with this trick, which leaves more than half of the turfs unaffected. I forget the exact counts, but it should all be documented somewhere in these forums.
Variations of the satchel trick can be used to add gang density to any zone, but you need to have enemy gangs with sufficient density to attach grove turfs. So think ahead before taking over all the normal turfs. Glitched turfs will not have enough density.