The wheels on a bag are extremely important. Better bags have higher quality sealed bearings, far more robust fittings, and are just better put together. I've used B&R Baseline bags for about 15 years now, they're pricier but the quality is top notch.

My 20" two-wheel rollaboard has the side handle and I think I may have used it once. But I use the wheels every single time out. For the OP, get the Travelpro - no question about it. Or look at B&R or Tumi.