Packing cubes are fantastic for organization. Separate your socks and stuff in one, shirts in another, toiletries in a third, etc. You can get the vacuum sealing kinds for slightly more, though I'd counsel against these since you'll inadvertently end up packing more, and by extension potentially go over a weight restriction if you check a bag or carry it all in a backpack like I do. I used to do the whole "roll clothes and stick them in" but I think packing cubes have made life a lot easier in terms of dividing up a bag into sections, so you can selectively pack (e.g. all winter clothes in one cube, swimsuit in another, etc.) and then rotate based on what you need. I actually live out of packing cubes even at home now, full-time. The only (very minor) complaint I have with packing cubes on the road is ... where to put dirty laundry, but that's a very minor complaint.

As for packing in general, it takes me around 15-20 minutes tops, mostly to fold clothes if I'm lazy. I have a dedicated travel backpack that I use whether it's 1 day trip or 1 month long trip. Inside, I'll have what I call a "tech dopp kit" which carries chargers, cables, etc. and I rotate that into my daypack for work or exploring a city. I keep a permanent set of toiletries in a clear bag from Tom Bihn and then restock as needed. This never leaves my bag. Clothing I'll rotate into cubes as needed as described above. If you're into souvenirs, you can half-pack a rollaboard (or bring it on empty) and gate-check it for extra space on the return leg. Also, don't forget to include a snack (granola bars are great for this). You never know when you might get hungry. Same goes for a water bottle -- a lot of airports have water bottle filling stations now (e.g. SFO/ORD).