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
Resistant hypertension is defined as high blood pressure that remains above a target level, in spite of being prescribed three or more antihypertensive drugs simultaneously with different mechanisms of action. Failing to take the prescribed drugs, is an important cause of resistant hypertension. Resistant hypertension may also result from chronically high activity of the autonomic nervous system, an effect known as "neurogenic hypertension". Electrical therapies that stimulate the baroreflex are being studied as an option for lowering blood pressure in people in this situation.
Unfortunately, this seems like a common scenario — medical guidelines recommend more aggressive medication use for minimal potential benefit despite potential harm. A new study published in the Journal of the American Medical Association (JAMA), suggests the blood pressure guidelines go too far for low risk individuals, and the risk of harm outweighs the potential benefits.
Lifelong control of hypertension will minimize the risk of developing heart attack, stroke, kidney failure, blindness, and a variety of other illnesses. Unlike other illnesses in which medications are taken for only a short period of time, high blood pressure medication is usually expected to be taken for the rest of the individual's life. It is uncommon, but not rare, that significant lifestyle changes can lower blood pressure readings to normal.
Hypertension is present in many people who are unaware they have this disorder. Hypertension is called a silent killer because too often the first symptom of the disease is a heart attack or stroke. To prevent this, get outside in nature and exercise, enjoy the flowers, and let nature provide a calming respite in life. Also, get regular medical checkups. If hypertension symptoms hypertension arise, seek immediate medical care. Call 911 immediately if someone has passed out unexpectedly.