Lone wolf programming involves many challenges as an individual must handle all aspects of development, marketing, sales, support, and more alone. Key issues include a lack of deadlines, no code reviews, difficulty testing for all bugs, needing to be skilled in multiple areas like coding, graphics, and audio, loneliness from working alone all the time, and the benefits of finding a partner or hiring help to expand beyond being a "cowboy coder" working alone in a "cellar."