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
If your blood pressure remains high for a long period of time, you run the risk of damaging your blood vessels. Your stroke risk rises significantly, too. And because your heart is working harder to push blood through your system, that very valuable muscle can become overworked and grow thicker. An enlarged heart causes further complications, including heart failure. Medications and special implantable pumps can help boost heart function. But if you can manage your blood pressure before it gets too high and puts your heart at risk, you may be able to avoid a lot of complications down the road.
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.