Josh,
Great post, and great questions. I cannot answer your exact question about returning to my 20s, because I'm only 27! What I can offer is this:
I live in Denver and am working on my third year in this beautiful, packed, and energizing city; Denver is wonderful and its easy to call home. I am starting a development, architecture, and construction business here in this city. What I have learned from being here is that anything is possible. If you commit to meeting people in the city, attending the right events, identifying the steps you need to take to get to your ultimate goal, then you can do and achieve anything you want to in Denver. I always tell my peers that Denver is the land of opportunity in the country of opportunity.
If I could recommend steps for getting started, I would say this. Find out what you need to accomplish to become certified in your real estate passions (agent/contractor/other). Find a mentor that you can provide services to that will guide you and teach you along the way. Find ways to market your name and your brand. The last thing is to start putting in the hours and focused attention to your work. All of this can be started before you move to Denver.
Good luck on the move, and good luck out on the field.