QUOTE(§ynchronizer @ Mar 27 2006, 11:14 PM) [snapback]1122775[/snapback]
My first play-through years ago I had to do it after Portland (Mafia - obvious) so I finished it in Staunton.
Out of the 3 islands it was the easiest, being flat.
Not only is it flat, it also has least gangs that attack you - the Cartel are dangerous, but Yardies, on the other hand, are pretty harmless.
In Portland you're in constant danger from the Mafia (lethal power - one good shotgun shot may blow up the ambulance), Triads (less harmful, usually carry pistols, sometimes only bats) and Diablos (harmless - carry bats only). Almost all territory of Portland is occupied by these gangs.
In Shoreside Vale there are Colombians (lethal, like the Mafia) and Purple Jacks (sometimes pistols, but usually bats). The Cartel are even more dangerous here (and will most certainly set your ambulance afire sooner or later) because they stroll up and down the climbing street with many curves where you can't hide and can't go too fast, either.