Chris, you'll LOVE Timberman, but know that although it is truly a world class event, it also can be crowded, which is both good and bad depending on your liking. Regardless, it is truly an amazing event. Know also that the course is tough, though most half Iron distance races in the northeast are indeed tough.
If you want to do Timberman, sign up the second registration opens. That obviously means you'll have to commit perhaps well before you are ready to make a decision. But if you want it, don't fret, just sign up. The fear of the distance will carry forth and motivate you to do everything you need to get yourself ready.
Yes, you will LOVE Timberman. Also know that if you do sign up, try to land housing fairly quickly.
