Properly planning your portages is essential for making or breaking your trip when out in the woods. As I usually say there are two different ways to pack for your trip. You either pack light and have easy portages, or you pack the more luxury items that provide greater comfortable on your trip, but also make your portages more difficult. Where this changes significantly is when you have either a lot of portages, or long portages. I personally enjoy bringing a cooler with me on some of my trips allowing me to pack better food. That being said I would not be planning on bringing a cooler if I knew that I had long portages on the trip. Another reason I like bringing a cooler is that it makes a perfect seat for the middle person in a canoe. Adding a third person to your canoe gives you advantages on portages as it is an extra set of hands. This person does not require you to pack many additional items and will provide an extra set of hands. When you add a forth person, you typically need to bring an additional tent and canoe, which would be the same efficiency as having two people.
You must take the time to think through each pack you will bring on a trip to effectively plan your portages. You should know how many packs you have, and if you will need to find a solution for other items like fishing rods or paddles. Items like rods and paddles can be easily secured to the canoe and do not add much extra weight to the person who is required to carry it. The person carrying the canoe can sometimes also take an extra bag depending on their experience. In many situations I have been able to carry both the bear barrel and canoe in one trip which significantly cuts down on how many trips you need to make.
The more portages you have, the lighter you want to pack. If they are all short portages or lift-overs then maybe you don't mind doing a few extra trips. If you have any long portages that go over 1-km you will really want to reduce how many trips you need to make. It is a good feeling when your planning pays off and you are able to complete portages with only one trip. It speeds up your trip significantly and also helps you to maintain your energy.