My friends and I did a play-through of DoS:2 Original as a 4-some. We enjoyed "just winging it" through all of Fort Joy and until we got off the first island. After that, it became pretty evident that we needed to consult wiki's or else we would hit dead-ends. For a while, we found it useful to find a map of encounters by level. That helped a lot, and didn't spoil things too much.
Eventually we hit a major snag: no one in the party had the scholar tag, and we could not proceed. We halted for weeks. Eventually, my buddy and I learned how to modify the game save file to add the scholar tag, and we were back in business. But from that point on, we kept a wiki handy to guide us through the rest of the game.
Overall we had a really great time. But it wasn't without a lot of frustration. I really don't see how you can have a good play through without consulting a wiki, unless you just have no life at all or you have access to a game developer. DoS:1 was pretty similar as I recall. I remember getting hopelessly stuck in the plot, until we learned that we had to go to a tavern in an obscure location and navigate through a seemingly endless dialog with an NPC that didn't SEEM important or noteworthy in order to progress.
Sorry for rambling. Bottom line, I recommend a balanced party with a variety of tags; make sure someone is dedicated to leveling up persuassion; enjoy exploring in the early parts of the game, but find a good guide to consult as you get deeper in.