Do I need to use canonical tags if I'm 301 redirecting pages?

[Omnipress]

I just took a job about three months and one of the first things I wanted to do was restructure the site. The current structure is solution based but I am moving it toward a product focus.

The problem I'm having is the CMS I'm using isn't the greatest (and yes I've brought this up to my CMS provider). It creates multiple URL's for the same page. For example, these two urls are the same page: (note: these aren't the actual urls, I just made them up for demonstration purposes)

http://www.website.com/home/meet-us/team-leaders/boss-man/
http://www.website.com/home/meet-us/team-leaders/boss-man/bossman.cmsx

(I know this is terrible, and once our contract is up we'll be looking at a different provider)

So clearly I need to set up canonical tags for the last two pages that look like this:

With the new site restructure, do I need to put a canonical tag on the second page to tell the search engine that it's the same as the first, since I'll be changing the category it's in?

For Example:

http://www.website.com/home/meet-us/team-leaders/boss-man/

will become

http://www.website.com/home/MEET-OUR-TEAM/team-leaders/boss-man

My overall question is, do I need to spend the time to run through our entire site and do canonical tags AND 301 redirects to the new page, or can I just simply redirect both of them to the new page?

I hope this makes sense. Your help is greatly appreciated!!

[RobertFisher]

Steve,

First, I am not a .net expert and there are some here. As to the overall question though, when you 301 www.example.com/boss-man to www.example.com/big-boss-man, you do not need the canonical on the example.com/boss-man. The 301 is handling all for you.

Best