If you clip a bird's wings it will not regrow the feathers until the next molt. If you clip during molt, you could have to clip again very soon, but feathers do not regrow once clipped unless they are removed at the follicle.
Always be careful when clipping that you do not cut growing (blood) feathers (covered in waxy sheath at the base), as these will bleed profusely. It is always a good idea to have a needle nose pliers handy when wing clipping for accidents - a bleeding feather can be yanked out, and it is easier to stop the bleeding at the follicle than from the end of a cut feather.
Do not let this discourage you from clipping. I find it an effective way to contain some of my birds. Feather clipping is painless for the bird if fully grown feathers are clipped, and the bird is used to being handled.
One other caution - I have had birds break blood feathers that I avoided while clipping. If you clip all the feathers on a wing, leaving, say, the one blood feather you find to finish its growing, that feather is then subject to damage when the bird tries to fly. I've come in to a bloody mess in the morning after a bird has whacked a blood feather off on a perch or against a wall. Since then, if I encounter a blood feather while clipping, I always leave a feather on either side for support until it finishes growing. Then you can clip all three.
As far as clipping one or both wings, this is individual to the bird. Very heavy birds can often be grounded with just a few feathers clipped from each wing. Very slim birds can often still fly quite well with all primaries and some secondaries removed! Some are easily discouraged by the "off balance" feel of single wing clipping , others learn to compensate and can still fly. You may need to experiment until you find what works for your birds. I always like to leave enough power so that if they do manage to get to a place a few feet off the ground, they don't sink like a stone on the way back down! Ouch!!
Most Zoos pinion their free ranging birds to keep them grounded - removing the last bone from the wing. This sounds barbaric until you consider the repeated stress to wild or semi wild birds from being handled multiple times a year, and the danger if the birds were to accidentally escape from that "one extra feather" finally growing in that the bird required for flight. Obviously, not a good option for adult birds, but done right after hatching, it could be a more humane option for birds you do not intend to acclimate to handling on a regular basis. It should always be done by a vet or bird keeper with the right equipment and experience.