After stripping the wax coat off of a leather shoe will acrylic paint hold without cracking?

Are you wearing it or making art out of it? If you're wearing it any paint will crack and acrylic will probably crack right away. If youre making art out of it it'll probably be all right though I would do several thin coats rather than any thick ones. You may also want to apply a clear sealer, which might even help if you were wearing it especially if you were only wearing it once for some special reason.