For the retirement accounts of course there's no tax impact.Thanks...appreciate your and @mongo thinking on this. I was partly asking to see if taxes played into your thought process. When I think about converting shares to LEAPs the eventual tax hit comes to mind (outside my IRA that is). This type of strategy would increase time risk due to theta as well as the need to make back whatever tax burden would eventually be incurred. This is what keeps me from converting long held shares to LEAPs. On the other hand, if you were holding shares currently at a loss at these levels it would make more sense to do the conversion.
I am leaning toward using profits from other strategies to buy LEAPs. These last six months or so have me a little hesitant to do anything that would increase risk to my core shares.
Where this matters is the brokerage account. I'm share heavy there with low cost basis - I plan to be selling share backed cc for the most part, with any incremental purchases of shares in the form of leaps. Down the road I may well find myself taking assignment on some of those shares, but only after I've been assigned on all of the new leaps I've been adding.