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: https://www.drugs.com/cg/how-to-take-a-blood-pressure.html
About This Image: Person receiving a blood pressure test. Medical research shows that as we age blood pressure rises slightly to accommodate an increased demand of oxygen and nutrients. It is completely natural for the first number (systolic) to be 100 plus our age. A recent study by a group of UCLA researchers came very close to corroborating Dr. Piette's guide for blood pressure of 100 plus your age for men, subtracting 10 for women, and this is after this rule had been in use for five or more decades. Are we now being taught that Dr. Piette's guide for blood pressure is wrong merely for drug company profit?
"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."