To or not to play Cover songs. If you agree wholeheartedly with the above sentiment and are a born rebel with a taste for adventure, then the life of a musician may very well suit you. However, even rebels must support themselves; even rebels have bills to pay.
If you play the same town every week, you’re over-saturating your market. You need to expand constantly. It’s unlikely to have a decent turnout at an important show if there is advertising for smaller shows in the vicinity that same week.