When it comes to Owl's Head, you'll want to consider the crossing if you want to stick to the trailed route. I know a rule of thumb is if the Pemi Gauge at Lincoln Woods is above 800/900, then the crossings can be difficult, in which case you might want to consider waiting, or taking either the Black Pond or Fisherman's Bushwhack to avoid the big crossings. Those Black Pond Bushwhack does save distance too, so it can be faster if you're confident navigating off-trail. There aren't book times for these stretches, so you might want to poke around for trip reports/GPS tracks to see how fast people can do it.