OK, I might admit that we have too many pieces of LL Bean luggage. We live near several outlet stores so it makes it possible to accumulate them without breaking the bank.
We have three of the rolling adventure duffles in the medium size and one without wheels. Definitely go with wheels. We also have one of the sportsman's duffles. It looks nicer but again, go with wheels. The mediums work fine if you're a careful packer. You can do a 5 or 6 day week in them if you're wearing t-shirts and shorts. If you need fancier clothes, jeans or winter clothes for the way home, you might want a large.
My dh has a slightly larger rolling bag from Bean's which still meets the carry-on guidelines. I can tell you that our four rolling bags neatly fill one Southwest overhead bin.
We have two large adventure duffles - they make pretty good ski boot and helmet bags - and when they're packed to the gills, they can be pretty heavy. (This is for two kids - plus assorted water bottles, gaiters, and miscellaneous junk.) You can also pack pretty much an eight day vacation for a large teenage boy wearing clean jeans, t-shirt and button downs every day in one of these.
The really large ones fit a very well equipped dive trip for two people, without the tanks, into one of them. Definitely go for wheels. One family can pack into it for a week.
The family size personal organizer is great, if you're driving. The new rules on carrying liquids and gels make it pretty much a no-go as a carry-on. You could probably pack it into another bag so that it was semi-rigid.
NHWX