I'm 5'11" and 165 lbs. and the HH Expedition is very comfortable for me. It's a great starter hammock, though the stock tarp really doesn't provide much coverage. If the rain's falling straight down though, it will keep you dry!
However, for $20 more, you can get the larger hex fly and they'll include the Cub hammock and two sets of snake skins. You can always sell the cub hammock or give to a niece or nephew (actually, I think you're getting the Cub and snakeskins even if you don't upgrade the tarp. Call them to be sure.)
And if your boyfriend will tolerate a used hammock, I'm sure you can pick up a Hennessy for much cheaper than $149.95 on this forum in the WTB section. Hennessy hammocks just don't have the resale value of, say, a Warbonnet, so they usually seem to go at a discount by motivated sellers (who are probably trying to upgrade to a Warbonnet).