So far, about 10 miles is the longest route that I have found for my commute to work where I am actually always headed generally in the direction that work is. To go longer, I would have to actually ride away from work. Natural obstructions and suburban roads ill suited for bicycles limit my choices. I like clipless, and don't regret buying them in any way. I once bought some shoes for $20, and I hate them. However, they came with cleats, so it wasn't a total loss. I am a fan of the rigid, stiff shoe bottom when using clipless. Spd moutain shoes are easy enough to walk into and out of work, and the double sided spd pedals are easy to clip in and out without thinking of them with some experience.