I was wondering how some of you do this conversion back to shares. I remember @adiggs did leverage or deleverage in a similar manner (shares->leaps->shares) IIRC so I'd like to ask him, but anyone else feel free to chip in.
Funny you should ask - I'm doing some of that this morning. You don't mention one way or the other - I'm assuming that this is an income oriented decision for you using positions that are open ended / roll-forever (that's what I am working with anyway).
NOT-ADVICE
And your question has me thinking multiple thoughts.
One idea that I've been going with - just sell some shares right now while the price is relatively high. I have an account with a higher fraction of shares than I really want right now as we approach ATH, so just sell shares and use that cash for selling (very conservative) puts.
Another idea that your question has me pondering - would I be better off selling really, really aggressive cc? Big up front credits and the shares are gone by end of week for more than an actual sale will net me right now, with the risk that I still own the shares at the end of the week. I think that I like this risk, especially on shares that are up $200 since I started the wheel with these 6 weeks ago (and that have no particular schedule for when I sell them - just income to collect along the way).
For those shares - STO 1100 strike cc for $48 (just did that). Mentally I just sold those shares for 1133 and am picking up an extra $15, with the risk that the share price drops from here and I get 'stuck' with the shares and the $48 credit. This works, in this instance, because I do want to own shares and figuring out the timing on when to buy back in on the way down can be tricky. If these finish OTM then I probably sell another week worth of really aggressive CC strike. Or the shares have dropped far enough that I continue owning shares and go back to selling my usual cc's.
Really aggressive cc like this solves the problem for me. The cash would enable selling really conservative puts. Those will be making a nice income but I'll want to stay way, way back so there is room for the share price to regress, and the income from these cc will be really good in the meantime (even if only 1 week). Heh - I probably just updated my approach to this one - when I make the decision to sell shares, use hyper-aggressive cc instead.
At low prices and a decision to buy shares, because I want to be highly biased towards moves up, I'll just buy the shares (leaps) rather than relying on aggressive puts change cash back into shares / leaps.
For the shares - leaps - shares transition; I'm still working that out. I think that most likely I won't be doing much of that - rather I'll be buying really far ITM calls at relatively low share prices and turning those into cash at relatively high share prices, with cash and put sales covering the in-between times. By DITM I mean buying 3 of those leaps for the price of 200 shares at max DTE (about the 450 or 500 strike today, but I won't be looking to buy until share price is more like 1000).
I anticipate holding a minimum of 1/3rd account value in shares / leaps at really high prices, and a target of 1/2. Even in ATH land. (And yes that means I'm trading in the possibility of opportunity cost by "only" holding 1/2 account value in Tesla at high share prices).