Thanks for the well thought out responses.
If i did my calculations right with the bankrate.com cd laddering tool, a ladder with 100k would generate about $1,000 per year or so. While helpful, that's not going to move the needle. Doesn't mean I won't employ it along with other cashflow tools I'm already employing, but I'm looking for something a little more revolutionary.
I'm looking for cashflow other than what I sell my time for in my job, money market or cd laddering to generate thousands of dollars of cash flow. I need about $25,000 to cover my expenses and be reasonably comfortable. Sure I could do less or more. My long term goal is to get to $40,000 of cash flow generated from investments without me having to work a single hour.
I'm looking for more security than the stock market. I believe there will likely be a fair amount of pain there over the next 4 years and am starting to take defensive postures to ensure I protect my capital with minimal opportunity cost.
Real estate seems to be one of the only ways to facilitate this type of cash flow based on the amount of stache I have accumulated.
My idea of high dividend stocks seems to be the second best option but you want to be diversified. So, for example, you can generate $20,000 a year in dividends on $400,000 owning say PM with a 5% yield, you could easily lose half your capital in a market correction. Clearly not diversified and as someone mentioned, you can get 1-1.25% worse dividends and more diversification elsewhere.
At my current salary, savings rate and expense rate, it seems I'm not doing something right or investing in the right places. My main options seem to be to continue to accumulate more wealth in the stock market and hope for 8% (give or take) RoR over the years and simply sell some of my taxable assets as I go. To feel comfortable there, and to generate $40,000 a year for the rest of my hoped for life, I would need about another $1MM dollars in the market. That would take about another decade if I don't factor in expected market appreciation.
Still searching for better options.