How do I clean up a 2011 iMac to prepare for a new iMac?

I have an iMac early 2011 that I’m looking to replace this year. It is my first ever Apple product so it’s highly disorganized, as I was getting used to a new operating system, coming from a pc. What can I do to prepare it for the switch?
I am still running Yosemite and I will likely keep both machines, though not sure how I will be repurposing the 2011. Thanks.

Personally, I would leave it alone, and just move things over as you discover (or know) that you need them. Over time, the things you don’t need will remain on the 2011 as a backup, and won’t clutter your new machine.

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I would make an attempt to roughly organize the data on the 2011 iMac. It doesn’t have to be perfect, but it will benefit from a general review and sorting. If nothing else, organize it into broad categories of Documents, Images, Pics, Videos, etc (for those pics and vids not in other libraries).
Copy all that 2011 data to an external harddrive and keep it with your new iMac.

I would also make a list and/or screen cap of all the apps installed on the 2011 machine. Sometimes you forget and it’s nice to have a reference. You can store that list on the external drive with your data.

When I migrate to new machines I usually put files in a ‘sort later’ folder… then tend to forget to sort them. On my Desktop I still have a folder called "Pile of Stuff 07-08’ that’s 225Mb with an almost unbelievable 2700+ text/pdf/webloc/gif/jpg files. Inside that folder is ‘Desktop Junk 2005’ (189Mb) that includes an iCab web archive from 2005 called ‘Tiger Migration Tips’, lol.(Okay, I just deleted that one.). Inside that is “•Temp•” which has some recipes I saved inside yet another folder called “Stuff 4-01”. (And inside that is a folder of files from Zip Drive disks from grad school from 1993!).

Why did I save an LA Times article from 2002 on LA dive bars? Why did I just find 3 pdfs comprising The Oxford Handbook of Aesthetics, apparently downloaded nine years ago? I don’t know. But it’s not hurting anyone and it doesn’t cost anything to keep it there, and doing an archive search some time might turn something up that ends up being useful…

So how would I move things over one at a time as needed? What does that process look like?

Also is Super Duper the way to back everything up? I do have a nas unit attached for backup and an additional hard drive where I do a super duper backup daily. Also, Backblaze. I feel pretty paralyzed to move forward, fearing I don’t have a box checked somewhere and something major will be lost. I run a small business which uses online invoicing, but the web portion utilizes my pics and videos.