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
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).
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.