Hey Mark - here's my take - others can likely give more or better info - but I've flown in there twice, driven up once (from SF Bay Area)
Question #1: will that leave us enough time/daylight/open golf course to get in a round that day, or should we just figure on a couple of hours of practice and the par-3 course mentioned below?
3:45 arrival into North Bend, I assume? It's a tiny airport and the shuttles are well-managed (btw, if you are flying, just do the shuttle - you will have little reason to leave the resort and thus won't need a car - that is unless you need or want to go to local casino or town of Bandon). In any case either way, best case scenario is you get to the resort at 4:45-5pm, I'd say. I'd guess it gets dark around 6:30pm at thje latest in October? So judge accordingly.
2: the flight back to Portland leaves at 11 something in the am? Does that give us enough time to get in one last round in the am? (I guess this is a pace of play question -- we're fast but if somebody's in front of us are we going to risk missing this little flight?).
you're really going to need to leave the resort by 9:30am to safely make that flight. It's possible you could fly around very early and get the round in, but you'd have to have everything break perfectly. Still, if you are early risers, why not try?
#3: Assuming we play 36 holes on Saturday and Sunday (the event starts on Monday), which course should we play twice?
ah, there's the great question, lots of disagreement there. But if you do have only the four rounds, it's hard not to do Pacific Dunes twice. It is the best of the three. Just how MUCH better it is than the other two is what we debate about here.
#4: Since we haven't been there before, I'm assuming that caddies will be of assistance?
I've found that it's hit and miss - some are great, some are not. I don't think a caddie is MANDATORY for scoring purposes... but if you do want to take no chances, then of course take one. They do add to the expense, but perhaps that won't be an issue for you.