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repotting progression

A lot of guides I've read describe progressing through several sizes of pots
until I reach the biggest size I want to use.

Is there any reason why I should keep stressing them like this?

If I ultimately want them in 5 gallon pots, why not go right to that size
when they are ready to transplant and just stress them the one time?
 
The reason is for better, more compact root development. It is ideal, but I always skip to the size I want, so far no complaints.
 
The way I see it, plants would rather be watered often and let to dry out between waterings. If you throw them right into a huge pot there will not be as much oxygen getting to the roots. Each time you transplant you also have the opportunity to bury the plant a little deeper to create a stronger/sturdier plant.
 
It is of my experience to just start them in small, small pots from seed and after the roots start showing at the bottom of the pot and put it in a 5 gallon pot to give it as much growing space and less strees enviroment that it needs.
 
I don't have any problem with going straight to the larger pots. I start mine in 16 oz plastic cups, and when they're ready to come out of there, they usually go into the ground. There is a lot more than 5 gallons of dirt around the plants in the ground.

However, if you want to stimulate early flowering, letting the plant get pot bound will probably help.
 
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