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.
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. 

The guidelines also redefined the various categories of hypertension. It eliminated the category of prehypertension, which had been defined as systolic blood pressure of 120 to 139 mm Hg or diastolic pressure (the lower number in a reading) of 80 to 89 mm Hg. Instead, people with those readings are now categorized as having either elevated pressure (120 to 129 systolic and less than 80 diastolic) or Stage 1 hypertension (130 to 139 systolic or 80 to 89 diastolic). 

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:
If you had previously been diagnosed with high blood pressure, the new guidelines don't affect you too much, says Dr. Conlin, as you still need to continue your efforts to lower it through medication, diet, exercise, and weight loss. "However, based on new information in the guidelines, your doctor may propose treating your blood pressure to a lower level," he says.
Blood pressure refers to the force exerted by circulating blood on the walls of blood vessels and constitutes one of the principal vital signs. The pressure of the circulating blood decreases as blood moves through arteries, arterioles, capillaries, and veins; the term blood pressure generally refers to arterial pressure, i.e., the pressure in the larger arteries, arteries being the blood vessels which take blood away from the heart.
I just started using high blood pressure medication and purchased a blood pressure meter at age 72. what concerns me is that the BP readings I get have a very wide variance in. I measure every morning as soon as I wake up, while still in bed and prior to having any coffee. I take 3 or 4 readings. I have found that on any given day my reading can vary from 126 to 143 systolic and the diastolic reading from 68 to 87. this wide variance makes it very difficult to track trends. My questions are: is this normal? is my instrument possibly defective? How can my cardiac doctor make a decision to put me on life long medication based on SINGLE reading in his office?
The guidelines also redefined the various categories of hypertension. It eliminated the category of prehypertension, which had been defined as systolic blood pressure of 120 to 139 mm Hg or diastolic pressure (the lower number in a reading) of 80 to 89 mm Hg. Instead, people with those readings are now categorized as having either elevated pressure (120 to 129 systolic and less than 80 diastolic) or Stage 1 hypertension (130 to 139 systolic or 80 to 89 diastolic).
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.
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The new guidelines stem from the 2017 results of the Systolic Blood Pressure Intervention Trial (SPRINT), which studied more than 9,000 adults ages 50 and older who had systolic blood pressure (the top number in a reading) of 130 mm Hg or higher and at least one risk factor for cardiovascular disease. The study's aim was to find out whether treating blood pressure to lower the systolic number to 120 mm Hg or less was superior to the standard target of 140 mm Hg or less. The results found that targeting a systolic pressure of no more than 120 mm Hg reduced the chance of heart attacks, heart failure, or stroke over a three-year period.
Some heart attacks are sudden and intense, however most heart attacks start slowly with mild pain and discomfort. Most heart attacks involve discomfort in the center of the chest that lasts more than a few minutes, or that goes away and comes back. It can feel like uncomfortable pressure, squeezing, fullness or pain. Shortness of breath may occur, as well as nausea, or lightheadedness. It is vital to get help immediately if any of these symptoms occur.
She'll inflate the cuff to a pressure higher than your systolic blood pressure, and it will tighten around your arm. Then she'll release it. As the cuff deflates, the first sound she hears through the stethoscope is the systolic blood pressure. It sounds like a whooshing noise. The point where this noise goes away marks the diastolic blood pressure.
A nurse takes your blood pressure at your annual physical. The numbers are recorded and the checkup continues. But do you know where on the blood pressure chart your levels are? Are they healthy? Too low? Too high, meaning you have hypertension? If you have high blood pressure or are heading in that direction, you should know that hypertension is among the primary enlarged heart causes, and a major risk factor for heart failure.
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.
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.
Last year, new guidelines from the American Heart Association, the American College of Cardiology, and nine other health organizations lowered the numbers for the diagnosis of hypertension (high blood pressure) to 130/80 millimeters of mercury (mm Hg) and higher for all adults. The previous guidelines set the threshold at 140/90 mm Hg for people younger than age 65 and 150/80 mm Hg for those ages 65 and older.

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.