Hi there! I haven't seen your pictures but your story sounds almost identical my daughter's hemangioma on her lip. Our ped. said the same thing and although it is possible for hemangiomas to go away on their own, it is often necessary to watch lip hemangiomas more closely and possibly treat them due to some of the complications you mentioned. So I think it's great that you found this site and are investigating your options now. I know that there are some great doctors in NY...Dr. Levitin is one of them, but I bet there are also docs who are closer to you. Maybe someone will chime in on here with a suggestion.
Here's my daughter's photo album with her lip hemangioma if you are interested in seeing it.
Every hemangioma is different and so it doesn't mean your son's will look the same, but I think you might be pleased to see the final outcome and know that it is all going to be ok. You are at the hardest part I think because it's tough to figure out what is going on and what the best steps are to take. I was always afraid to make the wrong decision. But a doctor told me once that there is no wrong decision....my daughter was going to be fine no matter what I chose and that really took the pressure off! With that being said, I'm glad that we intervened early because I feel like we prevented more invasive work down the road. We did not have propanolol available at the time because my daughter is 7, but it seems like a very good option.
As for the bottle problem, we had the same issue with bottles and nursing. She actually did get an ulceration from it. We ended up putting a layer of aquaphor on the nipple and on her lip to help prevent friction. That seemed to help the healing process and prevention of further ulcerations. Just a suggestion. Good luck with everything. If you want to chat more, feel free to send me a message here or I can give you my email address. It sounds like we might have a lot in common!