If you have high cholesterol does it mean you have to take cholesterol medication daily?

It depends. If you are otherwise healthy, high cholesterol can be controlled with lifestyle changes alone, such as weight loss and exercise. However, if you have other diseases in addition to high cholesterol, such as diabetes or coronary artery disease, your doctor may recommend starting medication. Each patient is different, and should discuss their options with their doctor.
Maybe? First get a lipid panel that shows the ldl-c (bad cholesterol), hdl-c (good-c) and the triglycerides (tg=little fats). The "total" is just the good+bad+1/5 of the fats, so it's a useless number. For example, if you have: LDL = 210, HDL = 40, tg = 100 that is a very bad total of 270. On the other hand: LDL = 140, HDL = 110, tg = 100 is a super healthy total of 270. Go to lipid.Org for more.
Sometimes. First, you and your doctor must decide if you should be on cholesterol medication. The most frequently prescribed regimen is daily. However, some of the current cholesterol medications on the market are broken down by the body very slowly. There is evidence that some of these medications work very well if taken every other day or in some cases even once weekly.