As a retail, I don't have to worry about OPM and my risk horizon is flexible. A different point: I find relative value so hard to determine when I tried to trade combinations instead of single/directional. A lot easier for me to "guess" if the underlying is going up or down. The odds are 50/50 with perhaps a slight up bias these days in a bull market.
Since the professionals, MMs and fund managers all know that B-S and normal distribution underprice tail risks, they can always price it in with enough "smiles" and "Skews". Why do you think they still "underpriced the tails"? I am not arguing with you, I am retail. Also, why the no arbitrage principle not priced in this tail risk?
You should save any residual value. Do not really believe the BS that most options expire worthless. Most options traders buying calls or put options close out trades that do not work and save the residual option values! They do not wait till all the premium is gone! Small losses are fine because once, you get a winning trade, you can make a lot more monies to wipe out those small losses all at once!
I use daily candlestick charts that end the 24 hour day at the NY Close so all overnight price action is included in that daily bar. Yes, I do want to purchase my option very close to the end of the trading session. If I entered at noon, the daily signal bar could look very different than it does at the close.
I tend to like long options as a short term rental. A few days to ride a trend. I view them like staying in a hotel as opposed to renting an apartment. Common wisdom says most options expire worthless, so I almost never hold to expiration. I take what I can get and get out. I also sell losers before they approach zero value.