We just finished a house about 16 months ago and it involved a straight pull of 3 wires 660'. I don't recall the wire gauge, but I do recall that the wire weighed one pound per foot per strand, or 2,000 lbs total.
Having it hooked up at one end makes no sense. That means you'd have to unwind all that wire and lay it on the ground and drag it into the conduit. We had it on 6 wire spools and did it in two sections (3 spools at a time) with a pull box in the middle. That was tough enough. On one pull, we faked out (unrolled) a spool of 300' of wire thinking it would slide through the grass/weeds easily. What a mistake. Once it was out, it took two guys just to move the single strand. Even on the spools, it took 3 guys, two feeding it into the conduit, and a guy on the other end with a 1,000 lb pull winch pulling it through. Pulling a maximum of 330', (even off 3 spools turning on pipe frames) was a tough job. If we tried to do it in one length, we'd have been handling 3 spools of wire weighing 700 lbs each, and pulling a total of nearly a ton of stiff wire through a conduit at one time. We couldn't have done it.
We used a 45 degree sweep to ease the wire into the conduit, and had no 90 degree turns.
Believe me, I didn't want to spend the money on the pull box, but it turned out to be money well spent. The advantage of a pull box in the middle would allow more bends.
That's my 2 cents, unless I misread your message. Good luck. Let us know how it went. How ARE you going to pull all that wire?