As for when to check your blood pressure, the most important thing is to do it consistently the same time of the day (ask the doctor which time he prefers and also what time in relation to taking your medication). The following article has a lot of good information for someone just starting to monitor their blood pressure:

Healthcare professionals use a stethoscope and a manual sphygmomanometer to measure your blood pressure. Typically they take the reading above your elbow. The sphygmomanometer has a bladder, cuff, bulb, and a gauge. When the bulb is pumped it inflates the bladder inside the cuff, which is wrapped around your arm. This inflation will stop the blood flow in your arteries. The stethoscope is used to listen for sound of the heartbeat, and no sound indicates that there is no flow. As the pressure is released from the bladder, you will hear the sound of the blood flowing again. That point becomes systolic reading. The diastolic reading is when you hear no sound again, which means that the blood flow is back to normal.
The brain requires unobstructed blood flow to nourish its many functions. Very high, sustained blood pressure will eventually cause blood vessels to weaken. Over time these weaken vessels can break, and blood will leak into the brain. The area of the brain that is being fed by these broken vessels start to die, and this will cause a stroke. Additionally, if a blot clot blocks a narrowed artery, blood ceases to flow and a stroke will occur.
If your blood pressure readings are consistently high, you and your doctor will probably discuss treatment strategies. Treatment for high blood pressure often begins with lifestyle changes such as a weight loss and exercise program as well as a low sodium diet. In fact, the AHA recommends adopting these strategies as a means of preventing the development of high blood pressure and heart disease. If these strategies are not successful in lowering your blood pressure, medications may be recommended.
Blood pressure readings fall into four general categories, ranging from normal to stage 2 high blood pressure (hypertension). The level of your blood pressure determines what kind of treatment you may need. To get an accurate blood pressure measurement, your doctor should evaluate your readings based on the average of two or more blood pressure readings at three or more office visits.
"Blood pressure guidelines are not updated at regular intervals. Instead, they are changed when sufficient new evidence suggests the old ones weren't accurate or relevant anymore," says Dr. Paul Conlin, an endocrinologist with Harvard-affiliated VA Boston Healthcare System and Brigham and Women's Hospital. "The goal now with the new guidelines is to help people address high blood pressure — and the problems that may accompany it like heart attack and stroke — much earlier."