Want to go bigger after uplift with implant. Do they have to cut the nipple again? (photo)

It is not possible to give you a medical opinion on your problem based on limited information and photographs. You need an in person consultation with an examination. However, it possible to make some general comments about what is typical or may be possible, but you should not consider these a medical opinion on your concerns. However, they may help you to understand potential options.
If someone is changing their implants for larger ones after a mastopexy augment it will require an incision to remove and replace the implant. A part of the existing scar can be used. This would usually be either the lower half of the scar around the nipple or part of the vertical scar of the lolly pop. Alternatively a new incision could be made horizontally in the crease under the breast as is usually done for a breast implant operation. This will leave a new scar but in a less visible area. They do not have 'to cut the nipple again'.
I advise you to have an in person consultation with a suitably qualified and experienced plastic surgeon to discuss your concerns and what may be possible.

Do not go bigger. You are already bottoming out from the weight of this implant. Your tissue cannot support more weight. If the areola is not being moved, no incision may be needed around it. Using the inferior incision, your tissue can be tucked up higher. Mesh will probably be needed for additional support.