When purchasing a hammock, one should consider personal style and needs, as well as usage conditions. If planning to backpack, most people want to go with the lightest weight options. Unless the user is claustrophobic or wants to keep all of his gear in the hammock, at your size, the Asym Backpacker, Hyperlight, Deep Jungle, or Expedition will fit. (All the same size, but in different materials and weights) Of those three, the Hyperlight is the lightest and most expensive. A good middle-ground is the Asym Backpacker, unless you prefer the lightest available option. If you are car-camping or traveling short distances, the Expedition may work for you. (I find it too bulky and heavy and usually carry the Hyperlight in summer.) Also, the weave of the Expedition allows mosquito bite-through from the bottom, so it needs a pad or a coating of permethrin spray. If you need more room inside, it may be worth the extra expense and weight/bulk penalty of the Explorer-sized models.
I like the bottom entry in summer, for quick escape from insects, and ease of exit/entry without a zipper to open and close. Also, it is easier to avoid getting the inside wet if it is raining as I get in and out. I might carry the side-zip in winter only becaue it is easier to deal with bottom insulation. If you will be using the hammock in cooler temperatures, the side-zip may be what you want. A lot of people feel the need for some sort of bottom insulation by the time the temps hit 50 or 60 degrees F. An automobile windshield reflector or a suspended space blanket may be enough with your sleeping bag at those temps. Air will be moving under the hammock to rob the user of warmth. The same happens when someone sleeps on a simple canvas cot. Try one outdoors without a tent sometime and you will quickly feel that effect.
Hennessy does not offer the combination of side-entry and bottom-entry together at this time. It would add both expense and weight. Most people like commercial hammocks for simplicity AND weight savings.
Happy New Year,