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No. You should however bevel (chamfer) the pipe end to prevent cutting or scaring of the rain collar as it is being pushed over the pipe.    
No. The Oatey Master Flash or Retro-Master Flash should be used in this application.
This question doesn’t have a correct answer because of many variables that could affect the life span of a flashing. Examples are extreme heat, extreme cold, and hail.
Oatey Master Flash and Retro-Master Flash are rated for continuous temperatures up to 212°F. All other Oatey flashings are rated for B venting, which are continuous temperatures up to 180°F.
100% exterior or marine rated silicone caulk can be used to seal plastic base flashings to the rooftop.
With the exception of the Master Flash and Retro-Master Flash, all flashings have a one year warranty from the date of manufacture. Flashings cannot be guaranteed for the life of the roof due to varying roof life spans, and potential adverse conditions (i.e. extreme heat, extreme cold, hail). If a roof is replaced the flashing should be replaced at the same time. Master Flash and Retro-Master Flash are the only exceptions; if installed properly according   to industry standards, they have a 20 year warranty from date of manufacture.
The size of the flashing is determined by the OD (outside diameter) of the pipe penetrating the roof or sidewall of home or building. Never try to slide a smaller flashing collar over a larger pipe because it will cause fatigue failure in the collar. Never install a larger collar over a smaller pipe and try to use sealant to fill the void. Any sizing miscalculations will lead to leaks within the home or building.

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