1 Option: Daily Stock Option Trading Blog and Option Education

Question Please indulge a beginner. I have limited myself to buying calls and puts until I got more familiar with option strategies. As February expiration approached I found myself hopelessly out-of-the-money (OTM) on 4 SHLD Feb170 puts. I'd bought them four months earlier when they were in-the-money (ITM). I had made money on some SHLD calls and I felt confident that the stock would retrace. Feb arrived and the stock had made its way up over $180. I had been watching it and it was not unusual to see it up $3.00 or $4.00 one day then down $2.00 or $3.00 the next. But, alas, I waited too long and there was no way I was going to see any profit and it was now too late to bail out. How does one get out of a position that has plenty of time but is far out of the money. I'm in trouble again and I wondered if I might SELL March 80 puts on JCP where I paid $5.50 for May 85 puts. The stock was down $4.00 today and I could have sold them for about $3.75. I would recoup some of my money, but they have plenty of time left on them. I doubt they will go far enough for me to sell-to-close at $5.50 or better. I read about your strategy to sell OTM puts for a little each time and do it each month. If one had a few months and could capture around $100 each time I might get closer to recovering my initial investment. Does this make sense?