Registration is expensive and cumbersome (requires fingerprints/background check, annual fees/filings, etc.) and seems like it'd be a huge turnoff (or a reason not to do convertible debt) for angels who do a handful of smaller deals (e.g. friends and family). Is it really necessary? Does it hurt the company at all if investors are supposed to register and do not?

(I realize the short answer to this question is to require your investors to have competent legal counsel, but I've gotten conflicting answers to this question when I've hypothetically posed it in the past to angels who I know are active in Silicon Valley. I'm bootstrapped right now and obviously would have my own counsel if/when I take outside money.)