Stock for stock, the only thing a 5speed has over an auto when wheeling is better compression control, which is useful for controlling your speed. The advantage the auto has is the torque converter, which lets you nose up to an obstacle and just throttle up until you get over it. If wheeling was the only criteria and a crawl box or doubler wasn't realistically going to happen, I'd take an auto.
But if you want the best of both worlds, go with the five speed and add a doubler or crawl box (or both). Crawling with super-low tcase gears is heaven.