I'd need to know the capital being invested to be able to answer this. If you have $100,000, the only way you're generating those types of capital losses is if the market tanks. I suspect that this is the type of money we're talking about, since you've sort of won the lotto as you said. If we're talking about generating $60k in losses off investing $1.5M in cash, that's a different story.
I'm inclined to think that this is a situation in which you just have to pay the taxes and do it with a smile on your face. Buying 30-50 individual stocks and trying to tax loss harvest will force you to essentially time the market on all of these stocks. Say you buy AT&T as one of your stocks. When will you sell to harvest losses? At a 5% decline, 20%, 50%? Will you be able to pull the trigger or will you think 'maybe it'll decline more' and wait?
Also, I think you might then be inclined to invest in riskier stocks, in an attempt to capture losses off that volatility. Here I think you'd be missing the forest for the trees and could potentially invest your way out of those profits.
Finally, private MLPs are essentially built for this reason. You get tax benefits up front to offset gains. I would really caution you on using these, as advisors get crazy sales commissions on these and they are very risky.