Startups and the law: tips for building a startup with hazy legal parameters?

I am building a product in the stock market / predictive markets / stock simulation space and find myself continually unsure of what is totally legal.

In seeking professional advice, I get differing opinions. Has anyone else had any experience in building startup in which they were unsure about its legality? I feel constrained; it is affecting my creative process - my ability to innovate. Does anyone have any tips as to how to overcome this?

I feel as though I need a lawyer who's aware of what I am trying to accomplish and who is willing to help me push the boundaries / manoeuvre around existing legal structures, but I have yet to find one. I am not in a position currently to pay one either. My concern with most lawyers is that they seem inclined towards conservative interpretations of the law.

I'd really appreciate some advice. Kindly, R