Interesting thread, good luck with it. I hope it's not only opened due to another specific discussion, recently.

But yes, some parts I handle similar. So instead of selling regularly to be invested at a min amount I use technical analysis and VIX to enter the trades. For selling puts for example I wouldn't prefer adding more puts after the market is going to a swing high and for short calls vice versa. I don't need to be in the market all the time and the argument that one has to time perfectly to find the right time is just a facade. It's actually easily to handle. I do momentum trades on ES-Future with my system and for longer timeframes, so I can use this to see whether shorting puts/calls is rather in my favor or not. One can be of a different opinion whether the outcome is better being most of the time in the market instead of timing it. I would think the outcome would be better but there's way more risk. But even if there wouldn't be a better trade at the moment than a really low premium trade with a short put, I stick to my risk management and better stay out of the market! Not finding a better trade doesn't mean for me to increase my risk compared to the reward.

The daily VIX-Chart is important to me, so I found a good way for me to short puts under specific circumstances. I do this for a few years now and treat this as just one part of all the things I trade. Doing only short puts or only options with my account I would never ever do. But this has nothing to do with fear, just the respect of the market.

Until last year also I did tons of shorting puts on stocks, risking to get assigned and doing covered calls to get rid until it starts again. At the moment I wait and see, the low VIX doesn't look that peaceful to me and market has shown that bigger doubts in Trump can shift the market very fast. So at the moment besides VIX and ES I sell premiums mainly on USO and there most times shorting calls (until last year both sides). The almost reliable "decay" of USO compared to CL is more than a small advantage for the bearish side. For ES these days people tend to say buy the ... dip. On USO I tend to state short the ... swing high.

That's tough to do. Not much into TA more fundamentals of the long term market, but it is important to sell on a down day or when the VIX has bumped higher

I don't do short selling, just shorting puts and calls as sketched above (--> Short-Put)

If you only sell puts, sure then a down-day can have positive impact, but imho often inviting too much unnecessary risk. Ordering the first lot for me would be fine to scale in but bigger moves can gain a huge momentum running far. I don't want to short a put at such an early stage. Too often waiting for such trades to have only a decent ROI and a lot of them actually need to be bought back to follow strict risk-management. Following the swings the ROI is way better and if not then the mid-term-trend was estimated wrong. I know lots of people do their options by just referring to numbers which is fine and has a long history but having a small edge (isn't that what we all are looking for) recognizing a hidden divergence, a shifting market, that can be worth a lot. Blending such possibilities out is (for me) like driving a car with only one eye.

As Ron mentioned, you are playing it very tight here. this is a trade you will need to monitor closely.

If you have a full time job, it would make more sense to place trades you do not need to watch too often.
E.g.: Ron's ES spread or Myrrdin's recent CL C60-C70 spread do not have to be watched too closely and can be done with a full time job.

I have a full time job as well. These types of trade do not take much time, give me more room and also offer good learning experiences.

With stuff that seems to be trending higher (relatively reliably), do you have a hard time with the short call side if you're doing IC's?

It seems like if you select your short strikes using delta, often times you still run very close if not breach the short calls anyway.

Perhaps these recent couple weeks aren't the case, but since we've had such low volatility and generally grinding higher, I find that putting on IC's is incredibly frustrating in this environment given the low(er) premiums associated with lower volatility.