Looks like it might be pretty good. Does it handle spreads? That’s the only thing I don’t have programmed into my spreadsheet yet. Though I almost never do spreads because I had a few scary moments trying to unwind/roll some that went bad.
Wingman handles spreads reasonably well. What I find is that as I open new positions I also spend a few minutes getting them correctly assigned together (these spreads). Sometimes it will add sold puts to a covered call strategy or vice versa. These are pretty easy to spot and easy to move. (Click the trade, click the Move to Existing option, and then click Here from the available open positions; or Move to New to start a new one).
It seems to do a very good job of assigning closes to open positions. Then later we manually move positions from the Open list to Closed.
It's not perfect but it makes it easy for me to get my positions created easily. It also, on spreads, tracks both the opening credit and the cumulative credit. I LOVE that.
One hint / suggestion that I've needed a month of transactions to figure out. Be liberal with creating new positions. WHen I started I thought I wanted a single never ending Covered Call in my account. Wrong
Instead when I open a covered call, any rolls due to being near ATM get added to that position. When it finally "finishes" as a winner, then it goes into Wingman as a close for the position, and I start a new Covered call with the next sale. The CC in Wingman is a "opening to winner" history. That idea applies to any position strategy.
I tracked my ICs as a vertical put and vertical call spread, rather than an IC. They can be tracked as an IC, but I manage the 2 legs independently, so this made sense to me. It probably works better to do these as an IC, with any rolls for time or incremental credit going into the existing position. And any new positions getting a new entry in Wingman.
The easy bit I want from analysis is my realized P/L for each calendar month. That's trivially easy. There is more to analysis than that but I haven't gotten into it.
It also provides the primary reason for these sorts of tools - a note making option where you can add whatever bit of text you want for each trade. I.e. what was the entry delta, why this particular position at this time. What was the alternative and why this over that - whatever will help you. The intent is to be able to look back and have the history that enables you to figure out when its working and when its failing.
After reading the last 20 pages, it is clear most of the traders here are much more aggressive than me. My TSLA objective is similar to yours, focusing on income/dividends and diligently managing risk. Growth is a nice bonus. Income goal is modest (maybe $2k/mth); anything beyond that is account growth. I’m aiming for making it as mechanical as possible.
My (intended) plan has two plays (tax free account, once I am offshore):
1) 4 x $25 OTM PCS -> Delta=15 & DTE=21-28. Repeat weekly
2) the Wheel -> DTE=7 & strike prices being +/- $50 OTM
Questions:
1) Is the 15 delta too unnecessarily conservative? Is 20 reasonable or a little too aggressive for an income play? Subjective, but curious of your experience…
2) I am basically layering 3-week puts every week for better premiums; I don’t think I’m adding risk to my plays, but welcome any clarifications from the more learned!
3) Do/have you consider adding a CCS to your PCS to increase income?
I am more comfortable with put spreads (mental block!?), but am thinking of adding CCS (but further OTM). In other words, an unbalanced IC.
1) I don't find it unnecessarily conservative. I'm landing more at .10 - .12. The challenge here is that the lower delta isn't necessarily the more conservative choice. The problem is that while collecting very small premiums, a single strong move against you can wipe out months of income in days or hours. With somewhat larger premiums you gain a bit of a cushion for those big moves. I haven't found a balance though where I'm reasonably confident I have safe income and some cushion with extra income to handle the losses. Losses will be in the mix no matter how far OTM one goes.
2) I like that layering idea - now that you mention it I am going to think more on it. What I'm doing right now is selling current week options for winners. I.e. if a put is winning, then I'll close it late in the week and open a new put for next week. Meanwhile any positions that sneak up on ATM / ITM get rolled. I don't mind turning a 1 week option into a 2 week, or even a 4 week option. As long as the strike + credit is big enough that the new position is a better one to be assigned at. I'll also be thinking about whether I'd be better off taking assignment to run the other side of the wheel, or just paying the piper and taking the loss. All 3 are available choices. I think I'm unlikely to push out past a 4 week to expiration no matter what - I would assume its going to assignment and reevaluate it week by week to see if a new roll has appeared that makes it worthwhile to continue.
3) I am considering adding a call credit spread. The margin is already consumed by the put credit spread, so they are "free". They aren't actually free - the call credit spread opens me up to incremental risk that isn't there otherwise. For now my thinking is that I might wait until 2 or 3 days to expiration and then see about a small credit on a big spread.
My mental model on my put spreads is that they are naked puts. I'll manage them like that anyway, even though they collect a smaller premium due to the insurance put I buy for them. That's why the very large spread - keep the insurance low and manage them aggressively (rolls down, and/or taking losses early). This is the side of the puzzle I need to figure out better - it's not a direct analogue to the covered calls.
