I stayed with my parents till I was 19 at which point my dad sat me down and said, "Steven, it's time to shit and get off the pot." Meaning I had to move on in life. They said I could stay with them but I had to pay then rent moving forward. That's when I applied to the university of Montana and (much to everyone's surprise) got accepted. I didn't resent my parents, they were right. What I resented was that all my friends at UofM didn't have to worry about things like rent or food money etc. I always had to work, sometimes two jobs and I wished they had helped more financially. All of that said, I knew that as an adult I never wanted to be without money. It was a motivator for me. I'm glad my dad "kicked me out."
Go. It's an awesome place and has some of the most untouched natural areas and old-timey, cowboy towns in the country. Montana is the real deal. I'd recommend spending a week in Glacier National Park, for sure. If you head out there, let me know and I'll be more specific with my recommendations, I'm sure scrimetime could recommend some stuff too as he was a roommate of mine out there. I'm pretty sure Fever (another old college roommate) still lives out there and I'm sure he could also steer you in the right direction. At the very least the three of us can advise you as to the best bars in Missoula circa 1999