OK, I'll bite and grab my calculator...
In your case you cannot split the conductors between two different conduits. However if I am understanding correctly, you only placed a 2" sweep through your concrete and into a trench right? That means you still need to dig a trench and lay the rest of the 500+ feet of conduit, assuming you are not going with direct burial, but instead aluminum conductors in conduit. Direct burial is fine, my preference is conduit though.
Voltage drop calculation:
for 100A (((0.0847/1000)*(525*2))*100)/240 = 3.7%
for 90A that's 3.3%
for 80A that's 2.9%
The 0.0847 is the resistance of 250MCM aluminum per 1,000ft per chapter 9 table 8 of the NEC.
Unless your AHJ has specific requirements, the NEC only gives guidelines, not requirements for voltage drop. Usually 3% up to your breaker box, and a total of 5%. The additional 2% would be from your breaker box to a distant outlet. So 250MCM aluminum get's you in the ballpark at 100A, but based on your shop size and listed loads, I'd say you don't need anywhere close to 100A, certainly less than 80A. At 80A you'd be under 3%.
Here's what I'd do, size the breaker for 100A, and if you ever do need between 80-100A, you'd just have more voltage drop.
For the wire sizing, I'd use individual aluminum THWN conductors in conduit consisting of 250mcm-250mcm-2/O-1awg. The 2/O would be the neutral and the 1 would be the ground. There's not much need to oversize the neutral so drastically since it only carries the unbalanced load. Technically, the neutral could be reduced, down to 1awg but no smaller. The ground CANNOT be smaller than 1awg because it must be sized UP from 6awg proportionately as the line conductors were oversized.
The wire areas of compact THWN aluminum conductors from chapter 5 table 5A for 250mcm-250mcm-2/O-1awg would be: 0.353+0.353+0.192+0.1352=1.0332in square. That fits in 2" SCH 80 PVC conduit which allows up to (40% fill) 1.150in2.
Brian