You should be able to suck all the solder out of a hole in one go with a Soldapullt. If that doesn’t work, you need to add more solder back into the hole and try again. You need to make sure that you heat up the solder enough that the entire mass of solder is one molten blob, so that it will all pull up at once. If some of it doesn’t get heated up enough, then it will tend to stick. Leaded solder is a lot easier here than lead-free. Even a mix of lead-free and leaded solder is usually a lot easier to suck up than just a bit of the lead-free stuff.