Depending on the overall condition of the roof- no sags, number of layers existing, etc, you can install metal roofing right over what you have.
We did this last fall on our place on Bear and it looks great. We used Forever Metal Roofing. We provided transportation (pontoon barge only, which you can rent from Sheps if needed). Their crew moves the material, installs and takes any waste with them, which was basically nothing as it is pre-measured and manufactured to fit. In and out in a day. If you truly need removal/disposal of your existing roof you'd have to get someone to handle that part separately.
For asphalt, reach out to Cody at Lake Life. He does them all the time. He is an island contractor and can handle it all. Also Ben at Island Construction.
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