Last night got the project started - which ended up - through the evolutions of this posting to be different than expected.
I had (as Eric_Phillips stated) decided to have only the power out to the barn - no other cables - anything else I would want will be "wireless"... SO I decided to use the existing 2" conduit... as we started to pull out the existing wires (CAT5, coax, and a horry story of a single Romex run... we noticed that there was water in the conduit - and by water I mean A LOT...
Now - this was to be expected, in retrospect - since when the conduit was attached to the garage there was no expansion joint - and the LB snapped off - on the side of the house that gets all the rain...
So - hooked the air compressor up and blew out all the water we could...
Then - to get rid of the rest that wouldn't blow out - we put rags on a rope - about 3' apart and ran 4 of them through the conduit... first batch did a great job - second batch came out clean! We decided it was a cross between a colonoscopy and cleaning a gun!
Anyhow - got the #2 out into the barn through the conduit - up the inside of the garage wall between studs in conduit... a hairy turn in the attic made and a 10' section in the attic run...
Tomorrow night we finish the attic for sure, run down the garage wall and break into the basement... anything more than that is gravy...
I could post pictures of gray tubing... but I know this group - you all can close your eyes and imagine it...