Lead pipe jacks (unlike neoprene pipe jacks) are quality components that last. Sure they cost a bit more, but the lead ones last and are attractive.
Lead comes in all sizes for all pitches, and a good lead shop such as A&B Sheet Metal can make custom units for those odd applications.
For power masts, they make a 'split' lead, which consists of two pipe wraps, one split in back and the other split in front. These are fastened with a stainless steel hose clamp similar to what is used on hoses attached to your car engine. Sand, prime, and paint these to match your new roof color.
The neoprene rubber pipe jacks are cheap, which is why most 'roofers' use them, but they will not last as long as any composition shingle on the market. Like an old Slovakian friend once said, “I’m too poor to be cheap.” In other words, don’t save a few bucks by buying inferior products that do not last.