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
Peter, I’ve been using a blood pressure meter for nearly 30 years, so my response is based on my personal experience and information I’ve acquired over the years. First, I suggest that you take your meter to the doctor and have them check several readings of your meter against theirs. For example, If your meter consistently shows it’s 10 points lower than the doctor’s, just delete the 10 points from your meter reading (have them check both numbers so you can adjust both as necessary). Also, it’s common that many doctor’s offices take your blood pressure incorrectly (you should actually sit still for 5 minutes, with your feet on the floor and the cuff at the same level as your heart) . Some of us have”white coat” hypertension, so you may always be elevated at the doctor’s office. If you are a large man, you (and your doctor’s office) may need to use a larger cuff as the wrong size of cuff can affect your reading. Also, I spoke with customer service at one of the companies that makes many of the home & professional meters, and she told me that the automated machines are not very accurate if you have kidney disease or heart failure (I have both). Ask the doctor’s staff to always use the manual system and it will be more accurate than those noisy automatic ones.
Your total blood pressure reading is determined by measuring your systolic and diastolic blood pressures. Systolic blood pressure, the top number, measures the force your heart exerts on the walls of your arteries each time it beats. Diastolic blood pressure, the bottom number, measures the force your heart exerts on the walls of your arteries in between beats.

Typically, more attention is given to systolic blood pressure (the first number) as a major risk factor for cardiovascular disease for people over 50. In most people, systolic blood pressure rises steadily with age due to the increasing stiffness of large arteries, long-term buildup of plaque and an increased incidence of cardiac and vascular disease.

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