I've been looking at some Clark models, but they're a little pricier than I would like. Some of the Hennesey models fall within my price range, but I'm not sure how I feel about the bottom entry. In terms of specifics, the most important factors to him would be: protection from the rain, protection from bugs, pockets to keep essentials within your reach while you sleep, stability (won't tip over in his sleep, but I think that's a given), and probably some aspect of comfort. He's about 5'9" and 175 lbs, so also something that works with his height and weight. I know these are really general specifications, but I'm totally new to this! I was hoping to spend around $150, but I would go a little higher, and cheaper is great too!