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Are there degrees of contentment? Can you be more content (or less) compared to other times?

To you, all you have seems small: to me, all I have seems great. Your desire is insatiable, mine is satisfied. See children thrusting their hands into a narrow-necked jar, and striving to pull out the nuts and figs it contains: if they fill the hand, they cannot pull it out again, and then they fall to tears.—’Let go a few of them, and then you can draw out the rest!’—You, too, let your desire go! covet not many things, and you will obtain. 

– From The Philosophy of Epictetus

I don’t think so. BUT would you agree that the opposite of content is discontent? And if anything is less than content, is it not discontent? I don’t know, but I do think you can be more content in a different way.

If you compare times in your life, it’s possible to say you are/were more content compared to another time, which means you aren’t more satisfied with life, but satisfied with more areas in your life. With who you’ve become, your relationships, the company you keep, the friends you have, the work you do, the place you live, your past, the decisions you’ve made, the lifestyles you have, the routine you’ve developed, the little things that you’re grateful for, what you have and what you don’t.

Is there an inverse relationship between ‘want’ and contentment?

Desire and contentment are completely opposed to each other. Basically if you want less, you’re more content (ie. in more areas). The less you want, the closer you are to contentment in all areas of your life.