You can donate three times a year to the red cross (once every 112 days). According to some page, you donate around 10% of your blood volume each time.
That means, for a volume equivalent of 300 people, you'd need to donate 3000 times, which would take around 1000 years.
The vampire is going to need more people, or to keep a person alive 1000 years with vampire magic.
When you're harvesting the blood iron of your enemies you don't have time for ethics. A controlled study managed 4 weeks within ethical boundaries, maybe we can cut that in half unethically. So 14 days, 3000 . 14 = 115 years. So when you torture two people, you could manage to do 58 years. Better start early!
You're off on blood production. "Safe" would be once every six to eight weeks for a pint. Plasma can be taken a lot more often. The red blood cells take a while to replenish.
But let's get real. You're not concerned about your enemy feeling well. Force them to take iron supplements and take a pint every other week. They'll likely stay alive that way. Fuck em, right?