Picture below shows plants at the size I transplant. I go right from the solo cups to 3 gallon.
I only transplant to a "middle" pot if I'm seeing any issues or if I over watered and issue doesn't seem to be going away. I will go from the solo cup to a 1.5-2 quart pot in those situations.
Transplanting into fresh medium can do a lot for a plant that's having issues, most the time it's all they need to get going.
I leave behind as much medium as I can when I transplant so it goes into mostly fresh soil/medium (moisture from the last pot stays behind), shaking the root ball will help break some of it off. I also like to "fluff" the roots before I plant them.
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