I've been on meds since I was 21 when I was in the best shape of my life as a collegiate athlete.
The important thing to realize is that it's the downstream effects of long-term hypertension that are dangerous...kidney damage, heart damage, etc. The good thing is that with proper control you will be no worse for the wear.
I am surprised he jumped right to medicating yuo, since you were borderline high, blood pressure varies all day long. That was one point in time. When mine was borderline high I had to wear a cuff for 24 hours that took measurements at set times so he could get a good look at my daily fluctuations. Yes it was a huge pain in the ass but medicating is also not to be taken lightly. The other thing is that with diet improvement (you mentioned it as well) you could control that without meds. Once you start on the meds there is little chance of coming off them.
Some docs will day that long term diuretic use can cause kidney damage itself. A nephrologist (kidney specialist) told me that and I guess my most recent physician agrees because he dropped my HCT dose from 25 mg like you to 12.5mg. I'm not trying to freak you out at all it's in all likelihood safe, however if you can control it with some diet and exercise it really is the best thing. Sorry for the diarrhea of the mouth but since I have it I've read up a lot over the years.
Best of luck