Since you mentioned pirates (as that one is pretty simple), let's start there. The most active times for pirates are on holidays and local weekends. Most of the frequencies will start to come alive after sundown, when propagation would make them audible anywhere in the darkness zone. Since there are a limited number of frequencies, it's not hard to flip across a few of them to see if there's any activity (I used to set up my RX320 to do exactly that). Keeping an eye on the popular mailing lists will give you a heads-up as to what activity *might* be coming up. Try to concentrate on logs no older than a week or two in order to develop a pattern. Try to avoid magazine based reports - they tend to lag 30 days or more from the time they receive a log to the time that they actually publish it. You want something much more current. I don't do chat rooms, but I wouldn't doubt there are a few devoted to pirate DXing as well.
Information is king in this hobby - the more sources, the better.
best regards..Mike