Gosh, that sounds like a lot of work.

Though I admit I have done sort of similar.

I have a bunch of long-term deep in the money calls, which in recent years forms my core long term holding. I roll them every couple of years, just a periodic chore like cleaning the gutters.

Separately (in my mind), when valuations seem high I write some calls. Usually a few months out, fairly close to the money. If the stock price rises more I roll those up and out in a roughly cash neutral way--eventually the stock price peaks and the last round expires. I make no money during the waiting and rolling, but the final round generally gives a nice profit.

Of course, during any moment that both of those things are in effect, and I have written a lot of calls (as now) I'm pretty market neutral: I'm long low-strike calls and short high-strike ones. At any given price (e.g., if the stock price is flattish), the high strike ones make more money each day than the low strike ones lose, so I make money.

Not so different from what you're proposing, just the lazy man's version of it.

A traditional option trader will say that this isn't smart because you have all the downside exposure below the low strike--but in that situation, I don't care about mark-to-market, I'll be too busy out selling a kidney to buy all the stock I can.

Jim