If you know exactly how to do things and you just need a laborer to help you or follow your direction, use your tools and supplies and you're not looking for quality work then $15/hour is certainly acceptable. If you don't know how to do the work, you're not paying for the workman's comp, insurance, unemployment etc, then your $15/hour guy is probably going to be finishing off a bottle of vodka on his way to your job and I hope you don't want paint free trim or straight rows of shingles cause you aint going to get it. As for $200/square for roofing...not in my world.
Most of the time you get what you pay for. If you want quality work, it's going to cost more. If you don't care about quality then ask Bill where he gets his "day laborers". If you don't know how to do this work and you need to hire someone who does...quit thinking in terms of labor since you now need to pay someone for their knowledge and expertise as well as their investment in tools, insurance, licensing, continuing education and alas, some profit.
Alternative, learn how and do it yourself to save the money...or is "your" time worth more then $15/hour?