Re: When would it be time accept you have high BP and need medication?
I would personally request that I go on BP meds if my systolic was consistently over 140 or my diastolic consistently over 90. But I'd make it clear to the doctor at the outset that I would continue on meds only provided the side effects were not too bad and that I considered this to be just a temporary measure until I was able to get my pressure reduced through lifestyle measures. IMO it just seems prudent to protect one's blood vessels while one is getting their act together.
I was personally on BP meds for five years until I was able to make enough lifestyle changes to be able to get back off them. But I had absolutely no side effect problems with my med (Lisinopril) whatsoever. Not everyone is so lucky, but there is no use assuming you'll have problems until you try it, either. But if you do, you can switch to a different med or make a decision to try lifestyle changes only at that time.