It's definitely true regarding long trackers, vs a storm such as Bob ('91). There is a propensity there for them to coincidently enter an eyewall replacement cycle near the latitude of Bermuda, after which, the trough that is approaching the EC (which is also necessary to capture in one form or another), imposes some kind of shear at a vulnerable time... Thus, the re-intensification prospects after replacement are irreparably harmed. Isabel is an example of this, but also had a random dry air insert near the GA/FL Coastal waters; that got involved and didn't help. Gloria in '86 did this, too... It was 155mph near 55W and when it was recurving it suddenly weakened to Category 2 or something less exciting like that..

Still, despite the climate behavior and the reasoning behind it... it is not impossible that one day something unique could transpire - as you also alluded. Think of '38 in New England, and Blue Hill had sustained 180mph winds because a category 3 hurricane was moving at nearly 50mph when it fisted into the bowls of SNE like astroid impact..