Both of the bows are about the same style. The outlander is a bit longer though, so that would be my choice for the first bow. The outlander also comes in 40 and 45 pounds which would also be what I would want for my first longbow. I can't say that I have ever shot the outlander though. There are quite a few people around that have the Montana that you could most definetely talk to. If you namethe bowin the topic heading, I'm sure it would attract them. Everyone seems to like them.
As far as the style of the bow, I love my HH styled longbows, they are my favorites. They are extremely quiet. But they are a bit shocky in the hand. The bows you mentioned I believehave a mild deflex/reflex to them which will help with the shock and you will get a bit more speed then the normal straight limbed HH bows. Below is a pic of my Schulz longbow which is also made in the HH style. It's 70" and 60#'s at 29".