CJ, welcome to the forum, you've made a good choice by taking your pool into your own hands! As long as the pool doesn't have a dog leg or 90 deg turn, 2 skimmers should be sufficient.
A larger pipe can pass more water, we run the plumbing to and from the pool w/ 1 1/2" and the filter system @ 2" to aleviate the loss from the water having to pass through the elbows, valves, filter and heater, I'm not sure how much it helps but in theory we should be passing more water through the system by stepping it up to 2". Sounds like your contracter knows what he's doing.