when to transplant these?

Hows it going everyone! So yesterday I got home and my plants looked pretty thirsty so i gave them a big drink with there first supply of nutes ( Alaska fish fertilizer from fish emulsion a 5-1-1 base) there about 13-14 days old and my other one has slowed growth it seems and had some tiny yellow showing on edges of the main leaves so figured they were starting to need some nutes... its was a low dose. BUT anyways I'm going in party cups and was wondering when most people usually want to transplant... I kind of want to go straight to 5 gals but heard it is easy to cause root rot or other problems since its to much soil to dry out for the roots...
<--- this one has exploded in the past 5 days or so .. was going pretty slow before that.

<---This was going great but seemed to slow down a couple days back... it looked pretty curled on the leaves and they BOTH were bone dry before i watered, not sure from the pic if u can see the yellow tips, The colyteons on both are almost about to fall off and are all the way yellow and curled.

in a week maybe 2

I transplant after my seedling has gotten sturdy so i know there is a nice root ball. Also i make sure undergrowth has started coming in. I try to never use time to judge my tasks for them, but i decide based on the girls.

I transplant after my seedling has gotten sturdy so i know there is a nice root ball. Also i make sure undergrowth has started coming in. I try to never use time to judge my tasks for them, but i decide based on the girls. I agree with above. Probably a week left and let it dry out for sure. The i take a razorblade to the bottom and split open one side and slowlytransfer to my hand. With the least amount of root manhandling

k THANKS for all the feedback guys.. that should work perfect ill go for a week ill be out of town with wife for a day or 2 before that so should work out great!
(there already smelling amazing lol could just sit there and sniff them all day!) undergrowth is barely showing on the smaller one but ya the bigger one has a lot getting bigger by the hour!

You didn't mention the age, but I moved mine from the solo at 21 days, cup was nice and full of roots, and within 3 or 4 days, boy did she show she was happy with the new home.
I went to a 2 1/2 gallon bucket, and just last night moved her into a 5 gal. pot.

I was out at day 16 and theyre flourishing