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It is difficult to tell from your photos exactly what is going on. A visit to your general dentist will put your mind at ease. There are many causes for the point going away. Your dentist should be able to he you.
I would suggest that you ask your general dentist or your orthodontist for a referral to a periodontist, a gum specialist, who could recontour your gums to make them less bulky and more esthetic.
Hard to tell from the pictures, but the first thing to do is have your gums checked and cleaned. Calculus or deposits under the gums can blunt your papilla's.
Rubber bands don't always need to feel like they are aggressively pulling your jaw to be working. Finishing an orthodontic case with rubberbands is about the finer movements and getting the bite just right. Be patient and follow your orthodontists suggestions. You will be happy you did.
Gaps between the two front teeth often are hard to keep closed....simple answer...we just bond (glue) a wire on the inside after the space is closed..simple as that!
Your profile will flatten somewhat but you probably will be happy with the change in the position of your teeth and how your profile looks after orthodontic treatment. You will not look sunken in from this treatment.
You upper lateral incisors, in a normal position, should be one half millimeter shorter than your central incisors. From your photos, it looks like they are in the correct position now. Don't be sad. This is normal.
I agree that you should absolutely not wear the retainers. Call your orthodontist on Monday and get a new set made.
I would certainly recommend braces for you. I would recommend getting the chipped tooth fixed after your orthodontic treatment.