Dracaenas, as a rule, aren't very picky about the soil they're in, as long as it drains quickly. The pot looks fine to me, except it would be better if you could lift it out of the saucer. I definitely wouldn't put the plant in a larger pot.
There is no reason why you shouldn't repot the plant. The only thing is that fall is approaching many areas -- I didn't notice your location -- and plants go into dormancy at that time. It's based on the number of daylight and dark hours the plant gets. It matters because plants use even less water during dormancy, so you will have to be even more careful not to overwater.
Be gentle with the roots. There will be a period of time after repotting during which they won't be able to absorb moisture from the soil. The plant has to grow new feeder roots first. The leaves may continue to drop during that time. That's about all the help ican offer. Good luck to you!
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