I think you get a good one or you don't, regardless of power levels. I talked to Bob today, he's willing to do my transmission, happy day. The ballpark number he gave me was even lower than what my dealer wanted, and his price included undercutting the gears.
I asked about a turbo, he's considering it but doesn't have his game plan together yet, he thinks it will be dead of winter before he does anything with it. I was considering upgrading to the 270 hp package while he had it, but I think I'm going to wait for the turbo and see what happens. Someone on the Rocket FB page had the 270 package, they said" imagine 30 more hp than yours" (mine), but their dyno sheet only showed 263 hp and 185 ft lbs (don't know what filter they're running, but I've not seen anyone else use the 1770s like I do), vs my 241 and 184, I'm thinking more bang for the buck with the turbo.