What you describe sounds like the ring gear is going. Pull the starter and turn it all the way around using a large flat blade screwdriver. You'll be able to examine the teeth. If it's bad, the trans needs to come out and the flex plate will have to be replaced.
If the teeth are good, the starter may need replacement (or it may just need proper shim adjustment). Proper shimming is very important on those starters. You can pull the metal cover on the engine side and see how the teeth mesh. Adjust with shims until they have just a small amount of free play.