Amp-Man
When I run 2 1/2" pipe for a service mast I usually drill a pilot hole trough the soffet and through the roof at an angle that is plumb the hole orientation is now straight with the house.
Then cut the 2 1/2 hole with a hole saw and to start keep the drill plumb to get the hole started through the soffet then climb onto the roof and do the same. depending on the type of clamps used for the pipe determines how far from the wall of the house the hole through the soffet is. once this hole is cut, I run the pipe trhough the hole and then line up the meter-base so all is plumb and anchor the meter base. I will pre-assemble the meter base with hub and adjustable fitting, if pipe is off wrt the meter-base its a simple matter of rotating the adjustable fitting to get a good alignment.
Then proceed with the wire and mast head and roof flashing.
We have around here what is known as a mast kit that comes with the Flashing, bootie, for the pipe and the mast head for 2 1/2 inch kit this is usually for 200 amp, there is a mast kit for 2 inch. But the 2 1/2 that is usually used for a long run of tri-plex of say over 120 feet otherwise we are allowed to use 2 inch ridgid.
Generally it takes one guy about 4 hours to put up a mast complete.