Good strategy. Also, if you are working from a 401K or IRA where short term vs long term capital gains are not an issue, you can harvest money from deep in the money leaps which are far deeper than necessary for getting the leap at near zero time value. For example I could sell a J19 120 call and buy a J19 150 call and maintain my same earning potential but have less money invested. I don't get a full $3000 per option back in the move because those 150s are still selling with a $3 time value, but if I sell my 120 leap at $313 and buy the 150 when the stock is trading below $310, I can often harvest $3000 per option. Today was a perfect day for doing this because throughout the day we saw an overall downslope to the trading and when half a million shares were shorted at Fidelity at noon, it strongly suggested we weren't going to see an afternoon rally.
The danger of using DITM leaps as shares substitutes happens if you ever see a nasty drop in share prices where the stock is trading for a prolonged period of time at a price below your strike price. That would be a 50% or greater drop for me. In such a case, you can't inexpensively roll your leaps forward to the next year's leaps. With stock, you just ride out a multi-year deep plunge and ride the stock back up when it recovers. Also, since DITM leaps are leveraged trades, you're best off leveraging when the stock is at a low point ($180 recently) than at a potential high point.
I subscribe to the Chickenlittle approach, which is to leverage into DITM leaps when the stock looks like it has bottomed out, and then convert those DITM leaps to shares before the stock reaches its peak. You're then riding up with a leveraged position and riding down with a deleveraged position. The tough part is forcing yourself to deleverage soon enough.
Firstly, my discussion does not concerns itself with tax consequences (I mostly use TFSA/RRSP accounts in Canada)
Now, I agree with most of the stuff you're saying.
Except that I can't reliably execute any of the strategies you describe
. If I could, such skill would lend itself to trading, which perhaps is more lucrative than investing. Anyhow, I don't do that (anymore).
When replacing options, I use multi-leg strategy that guarantees execution of both legs simultaneously, I just specify diff I want to pay. I can often trade at a median price of the spread. Multi-leg option execution is a rather new feature of TD Direct platform(not Ameritrade, or whatever you have down south).
And, mistaken or not, I hear in your reasoning assumption that this is a levered trade, implicit assumption that I'd use all/most of the capital.
I don't approach it that way. I start from the point that I figure how many shares I can afford and want to buy. Then I get corresponding number of contracts (shares/100). And there is 30-50% of the cash left, depends how deep in the money strike is. That cash gives me opportunity to lever, but that is not automatic decision by any means. It's usually separate in time. Last time I added significant exposure was on the March 23rd, when I played for the Ichimoku cloud bounce. But I can't do that consistently, so it was a bit of a gamble, if it dropped under 240, I'd have dropped that additional exposure and then some. Sitting around 130% now with some cash on the sidelines. Some of the cash I used for AMZN at around $800, lucky me
I do want to call in the fact, that if you don't leverage,
you will lose equal or less nominal $ by holding this kind of assets vs stock, so your description of danger is correct when you're leveraged, but otherwise it's not. Now, most ppl do this for leverage, but you don't have to.
For example(assume SP $300 for ease of calucation), If I buy 10 contracts of $150 strike TSLA, instead of 1000 shares($300K), I will pay around $150-$153K, deploy about 50-51.5% of the capital.
If stock dropped 50%, I would lose around 150K in shares, but probably around 120K in options, as options would recover some time value and be priced around $30 (price for Jan 19 if Tesla was 150 - sounds about right?)
Furthermore, if Tesla dropped to $100, I would have lost $200K in shares, and loss in options is limited to invested $150-$153K, but option would still probably be worth some $10, so loss would be around $140K
Taken to logical extreme, if TSLA goes to 0, I lose 150-$153K in options, but $300K in shares
So DITM calls are actually safer, if you don't leverage yourself