Facepalm...

[Fuzzy Dunlop]

Jool has moons, you can use them to flip the inclination of an orbit 180 degrees for very little delta-V

[AustralianFries]

Why not circularize near the altitude of Laythe, and when you get an encounter, adjust your orbit to where you can get an aerobreak on the far side. You should spin around the back (at a really high speed, but that's the reason you're aerobreaking) and get thrown onto the right path.

[Echostatic]

Other than Charon, Pluto's moons aren't worth mentioning. Also, even if you crashed all of Pluto's moons into it, it still would be slightly smaller than Eris (assuming our size estimates of Eris are accurate). It's hard to picture just how tiny Pluto really is; five Plutos stuck together would be a bit smaller than our own moon. For that matter, if you mashed every one of the 30ish biggest trans-neptunian dwarfs/moons into a single mass, that mass would STILL be slightly smaller than Earth's moon.

For comparison, Mercury is about four times the mass of our moon, and Earth is 80 times its mass.

So what you're saying is, we need to mash all of those dwarfs and moons into a single mass, and maybe cut chunks of mars and venus out and smush them into it too? We could call it Super Pluto.