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Time to Repot?

I bought a N. Coccinea back before xmas and it had four 2 ft vines coming out of a 8" pot I cut all the vines off and let the plant restart with basal shoots, now there are about 10 shoots coming up from the 8" pot and about 20-30 new pitchers what I'm wondering is when should I repot it-it looks very crowded in the pot and appears as if I could divide this into several plants in 8" pots but it's growing so well I don't wanna shock and/or kill it either!

My N. ventricosa on the otherhand seems stunted and isn't doing well, the leaves start to come out then stop developing at about 1" and then another starts to come out. I can see the roots at the bottom of the pot because it's rooted in a 32 oz clear deli container. Would need of a new pot cause new leaves to develop poorly?
N. Coccinea = lowland
N. ventricosa = more highlanderish
That could be your problem
I let some more experienced nep growers answers the other questions
well the coccinea is doing real well the only "problem" is I fear it may crowd itself to death in the pot as there's about 10 shoots coming from the substrate-can I or must I divide this into several large plants?

Also do Coccinea produce upper pitchers? I have a cutting which has grown a couple large leaves but is not yet pitchering. Does it take a year or so for a cutting to establish and make pitchers?
Hey swords. Are there more than 1 Nepenthes Coccinea in the 8 incher? And how long has it been in there? Whoops I see now! Back before Christmas ehh? Hmm.....I would say you can repot if the pot is overflowing with TONS of pitchers and/or there are roots coming out of the bottom drainage holes. Your N.Ventricosa should be in intermediate/highland setup. Don't worry about geting it too cold either as I have mine in an Ultrahighland setup up now and it is a SUPER vigrous plant under the Ultrahighland conditions. ultrahighland conditions are for the Rajah I have BTW. And yes ALL Nepenthes cuttings/plants produce upper pitchers in thier life. It just takes quite a while unless you have a plant of N.Gracilis in super lowland conditions!!!