Yeah sometimes those "woulda couldas" haunt you for a while. I had 80 Oct BRL calls in spring 2008 when the stock tanked on what I considered fundamentally irrelevant news. My plan was to hold them for several months (they were 5 months out) because I was certain the stock would retrace most of way back, but it would take some time. I sent my husband an email about the trade and said "this one will net us $120K before the fall". Moved in my favor immediately and as soon as it started its first pullback a couple weeks later, I closed the position for an $8600 gain, figuring I'd take profits and get back in again when it retested that low. It did retest that low while I was on vacation a little over a month later. A couple days after I got back BRL was bought out at a price $20 a share above my strike and would've netted us $144,000. So do I pat myself on the back for taking the profits instead of letting the position draw down and holding/hoping? Or do I smack myself for failing to trade the plan? (Or do I tell myself that as a trader one should never take vacations unless one will have uninterrupted internet access?)
Your question is neither trival nor naive, too many people who trade options ( long or short ) lose every penny they put in. As a rule for long options, your rule is very sensible as long as you can stick to it no matter what.
I had the same thought about being away on vacation without internet access. That gig is for investors