Will upscaling or using clone stamp/healing brush to upsize give better resolution?

I'm designing a 5.25" square CD cover using a rectangular image and the resolution needs to be min. 300ppi to print .  The artist sent me the art image (painting) from her camera as a jpeg and it goes to photoshop as a large (approx 20" X 24") file at 72 ppi.  To change the ppi to 300 without resampling (I've been told this is best), the image becomes too narrow (4 1/2") and too high (5.9"). 
I don't want to crop because I don't want to lose content.  I want the image to completely cover the CD cover  And I want to keep the same proportions for certain parts of the image.  So I believe my two best options are as follows:
1.  Bring the image to 300ppi with the measurements above, protect certain parts of the image on an alpha channel, content aware scale the rest of the image wider to make it square and then resize down a bit for the CD cover or
2.  Bring the image to 300ppi and then use the clone stamp and healing brush tool or content aware fill (doesn't work so well on this image) to duplicate and extend the sides of the image to widen and square it and then resize down a bit for the CD cover. 
Does anyone know which of these options will give the best resolution?  Is upscaling more likely to cause pixelization than the other option?  Is there a better way?  Should I do options 1 and 2 to the large 72 resolution image instead of bringing it to 300ppi first and then upscale or clone stamp--would that give better results?
Thanks, any help is greatly appreciated!

You've said that you don't want to crop, and you want to cover the entire CD cover. That leaves you with two choices. Extend the short side(s) via cloning, content aware fill, etc. or stretch the image in one direction, either with the standard free-transform or with content aware transform. See what looks best. Your resolution will be fine. You can res up if you need to. The amount you're short will not matter here. Leave room for bleed - usually 1/8".

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