Thanks Misterkel, more ways to play with options.it seems like I have a lot to learn and ponder. And hopefully, not getting burned doing it. What do I need to know more to execute this? How much do I need to understand the Greeks (I only understand the definition and not versed in interpreting them)?
You need to understand Delta to an intuitive level so you don't need to check it. Delta is used as a proxy for likelihood of outcome, too. A .7 delta (almost certainly In the Money) has a 70% chance of expiring In The Money. A .2 Delta has a 20% chance. And so forth. A .5 delta is typically ATM, regardless of time to expiry.
You need to understand Implied Volatility and get an intuitive relation to it. IV has the greatest effect on option pricing (although it's IV IS the effect really). IV moves dramatically with events. Earnings coming up strongly increases IV. IV is dramatically higher for the first expiry after earnings. There are ways to play differential IV - calendars and diagonals. These are much more sophisticated plays and can be used in non-directional manners. Meaning - if the stock goes UP, you win, if it sideways, you win a bit less, if it goes down very slightly, you can still win. If it goes a moderate amount, you break even. If it tanks, you lose.
You need to understand Time Value (also called Premium).
You need to understand liquidity at different levels of the option chain. Bid-ask Spreads and Open interest are the best measures of liquidity. SPY is the most liquid option chain in the world, most likely. Though SPX has daily expiries, so - pretty liquid. Time value decays at different rates, depending on expiry. Long expiries have very small decay. Near term expiries have very rapid decay. So, you can do Calendars or diagonals to capture the near-term rapid decay, while hedging with the longer dated. BUT - time value disappears as the stock moves further from strike, and longer dated options lose more to this effect than near terms because near terms have much less time value.
You need to understand Theta, but the theta values given are often quite inaccurate.
AND, study option structures. Synthetics are very good for using less margin to hold a position. In other words, if you want to hold your stock (non-div stocks work better) for price appreciation, just buy call and sell a put. You can do it ATM or almost anywhere in the chain provided you buy and sell at the same strike. You can do it long-dated or short dated. Outcomes are the same as owning the underlying provided you have Put-Call parity (same time value for each option essentially).