You have the right idea_ you want the medium in the cup to hold together as much as possible_ you don't want it too wet or too dry_ it should be moist but not wet or dry.The type of medium_ soil, coco, or whatever mix you have going_ its hard to tell from the photos_ but it looks like some type of soil mix_also will affect how well it holds together. How well the roots are developed and have grown into the medium_ will make a big difference in how well everything holds together too. Thats why folks recommend waiting until the leaves have extended out to the edges or a little beyond_ so that the roots have time to develop. You want them to basically grow out to the sides and bottom of the cups but not much more than that_ definitely not to the point they become root bound. From the photos it looks like you have some in cups and others in larger pots. The ones in the larger pots have a ways to go before you transplant them. If you have to dig them out then you'll damage at least some of the roots. Even the ones in the cups could go a few days longer at least. When you decide to go for it first try the largest plant in one of the plastic cups. Take a pair of scissors and carefully slide the bottom blade down the into the cup on one side with the other on the outside. Then cut through the cup to the bottom. Hold the cup in your hand at about 45 degree angle, peel back the plastic so you can get a look at the roots/medium. the medium should kinda hold together and keep its shape and you should see some small roots along the outside. If the medium starts to crumble apart its too dry or too wet. Obviously if water runs out then its too wet. Tape the cup back together and wait until the moisture content is right. When they are ready I cut down two sides of the cup, peel back the plastic back between the two cuts, turn the cup in my hand until the medium rolls out into my hand and then move it over to the larger pot and gently place it in the hole in its new home. Gently pack the medium around it to hold it all in place. Once I have the seedling in its new home and stable then I just tap the pot on the floor a few times so everything settles down but doesn't get packed too tight. The soil in the larger pot should be moist but not wet. A few hours later I spray the surface with a root stimulator in water PH to 6.0. This helps the roots to recover and get busy growing. If everything looks good the following day you've done good by her. Repeat as necessary for the others when they are ready. Good luck_ hope all goes well and that this helps you somewhat. Hydro Guard is a good rooting nutrient solution. And not expensive.