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The best times Ive had with the game have had nothing to do with missions, I spent most of my time just in the open world. Its the sheer random factor of not knowing what happens next. Helicopter battles, sniping from rooftops, drive by wars etc.
There was a full on tank battle in my game this afternoon. Mercs were being called in, Attack choppers, Jets all sorts of shit. It was glorious.
The most fun I had in free roam was a spontaneous free roam death match that involved 6 or so people, two with bounties, on the interstate. Semi trucks with trailers crashing everywhere. Heavy police involvement. It had me laughing my ass off the whole time.
But when it was all said and done, I'd lost ~20k because of the penalties of dying in free roam.
After that I stopped involving myself in the most fun GTA online activity.