And finally, I've done a few installs with that thick wire. Feed it into the conduit on the ground using LB's and dull tools...then use the conduit as a lever to bend it up to final position. You will learn some new swear words regardless of how you approach it.
Yeah, it's going to be interesting feeding three #1/0 (two hots and neutral) and one #2 (ground) through approx 100 feet of conduit. I have about 40 feet to run underground from generator to foundation, then 9 feet up an exterior wall, then 40 feet across an interior wall, then 6 feet down interior wall to panel, with a few turns here and there. See attached image, which is a top-down view from above. Trying to strategize the best way to do it, where to start, where to end, etc....
The underground and exterior conduits will be glued up ahead of time. For the interior, I may just friction fit the conduit together one at a time, sliding it over the wiring as I go. Though I have the option of running through a "raceway" for the interior portion, and I need to learn exactly what raceway means for residential code. Seen everything from cable trays, closets, and wall openings defined as raceways on the industrial side.
One strategy is to start at the halfway point and feed wire through the 9' vertical and 40' underground legs towards generator, before I swing the whole assembly up toward the exterior wall. In the process of doing that, I can start feeding the remaining cable through the wall into the interior and at the end swing the vertical up and affix the LB to the wall.