I wrote about this topic a bunch here: http://www.seomoz.org/blog/white-hat-seo-it-fing-works-12421 but basically, I ask myself a number of questions:
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What are my goals in web marketing? Is it purely to make the most money possible? Am I trying to build something bigger than myself? Something that will make people happy? Something that can last even if I'm not around?
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Do I want to prioritize the short term or the long term? Can I afford to make more revenue, get more traffic in the next 6 months, if it means the 5 years after that might suffer?
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Do I want to work on building a brand and a company and a product or just a website that gets traffic?
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How much stock do I put in Google's webspam team vs. my ability to outthink them? Do I have the mental discipline to withstand the nervousness, doubt and fear that comes with spamming/manipulation the engines?
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Do I think that spam and low quality sites can convert at the same rate as a high quality brand? If not, does the delta make spamming non-viable, even if my only goal is revenue?
The answers to those questions for me are clear, and they're what's led me to always pick white hat for the projects I do.
Hope that helps!
If I had to guess, I'd say sometime in the next 2 years, but not anytime in the next 9 months. We've stopped asking the team for a final delivery date because it's just too hard to estimate all the work required, and past estimations have been so far off target. Instead, we just try to estimate the next quarter worth of sprints and then measure how we perform against those.