Hi Mike,  One approach that may be useful is talking to a mentor who could offer you specific guidance on these questions. Another great resource is SCORE, one of SBA's resource partners. SCORE is a nonprofit association comprised of thousands of volunteer business counselors throughout the country. They are trained to serve as advisors and mentors to aspiring entrepreneurs and business owners (at no cost to you). You can find your local office or set up an online meeting to chat with someone about your questions.