My basic investing goal is probably similar to yours. I want to produce enough cash each month to pay the bills, have some fun and to grow my investing base thereby increasing the monthly cash flow so I can pay the bills, have more fun and grow my investing base and so on, ad infinitum.
To accomplish that goal I currently need about a 20% average annual return on my investing base. Again, see my General Investing Philosophy to see how I currently try to do that.
A secondary goal is to accomplish the basic goal with a minimum of fuss and concern. Ideally I could do that with a good collection of stocks that pay a 20% dividend. Since we all know that is not going to happen I need a back up plan. So, the back up plan is to build up a good (that’s a subjective term) portfolio of stocks that pay a decent dividend and to sell out of the money covered calls on the portfolio. As the investing base grows I can rely less upon selling puts and more upon selling out of the money covered calls. Collecting dividends and monitoring covered calls both generally reduce the fuss and concern (risk) associated with selling puts.
A third goal is to provide for my wife if she outlives me (I am almost 6 years older so there is a good chance she will). Since she doesn’t know and has shown little interest in learning what I do with the portfolio, I need to accomplish my second goal, or at least come close to it, sooner rather than later.