The problem with threads like these is that you're attempting to publicly reconcile being unsettled by the drop. This is not a "value" market. Look at the public fund performance by value investors in recent years.
If the goal is to trade vol then understand your market. Don't roll monthly. It drives me nuts when ppl short weeklies or 30-days out for "vol" exposure. Short quarterlies. Overwrite. There is no point in buying shares and writing a 1Y call... short the 1Y put. I realize that you're not explicitly in these names to write vol, but I'd bet that you're writing calls on a large(r) minority that you'll admit.
You're a good dude. Why CC when you can short a put? Because your truly a believer in the market going forward? If so, then forget vol entirely or get some knowledge. You want to hold XYZ for 3-5Y? Short 3 to 1 in the 1Y calls at 20 deltas. You're still 40D long. You want three times the spot-exposure? Buy 300 and short 9 of the 20D.
More conservative? Buy 100 XYZ at 200 and short two of the 1Y 300C. There is nothing to think about; you're neutral to the synthetic (near $300). No way you're not up on marks at $300 any time prior to expiration. There are outs at that level which include covering at sizable gain, buying the wings to effect a long fly at a credit, etc. The point of this (synthetic straddle) position is that it's automatic; you know from day1 where you peak profitability lies, regardless of vol. One benefit is that it won't make you the weak holder and you'll benefit from the tax deferral if you hold into the OpEx year.
You start with a wrong presupposition and you get a wrong answer...One size does not fit all. Let's go to Edward Jones and have them run an analysis of what I need for retirement!! "The computer readout says you need loaded mutual funds and a couple of annuities"!!
I've shared my situation before, so I'll just repeat it briefly. Have a lot of money with no place to put it. Yeah, some is in CDs...I'm 65 1/2. Have investments spread everywhere; house, rental, investment lot, tons of stocks, CDs, note and deed of trust, 5 ROTH IRAs (my wife and I), gold and sliver coins, vehicles paid for, life insurance, ect.
I have a ton of assets, but very little income...About $70,000. this year. THAT IS OK...I am spread everywhere for asset protection. What I don't have is a trusted second person. My wife is wise and has a good business mind. She doesn't want to deal with investments...Would rather play with grand kids. It is her choice and I respect her for that. If I passed away or became disabled, someone would have to step up to the plate to exercise those puts. My wife doesn't want to deal with it. My kids have kids and can barely keep up with them. One is in town and not responsible...The other is out of state and is responsible. If and when my wife and I become incapable of handling our investment, it will go to a bank's trust department to make the decisions. They may not look at our accounts at Schwab and Fidelity for months. They may not catch having to clear/fill positions!! DO YOU UNDERSTAND!! I've had two heart attacks, my wife has had two hip replacements. I can manage the assets now, but in the future there is no way to know what will happen. The trust department will take 6% per year to manage our affairs...Plus using their accountants, Realtors, lawyers!!
If I (or my wife) are in a rest home, we hand it to the trust. But, we will make more by having $100,000. sitting in a money market account at Schwab/Fidelity (earning diddly squat) than having the trust department grabbing the 6%!!
Again, covered calls make sense for our situation...And again, it's only 10 to 15% of our portfolios. For 95% of the people out there it does not. Agree to disagree...
I see nothing untoward.