Answer
(Fatwa: 1840/278=B/1429)
(1, 2) It is mentioned in Fatawa Alamgiri:
ولو أدخل إصبعه في إسته والمرأة في فرجها لايفسد و هو المختار إلا اذا كانت مبتلة بالماء أو الدهن فحينئذ يفسد لوصول الماء والدهن
It means that if the glove is dry and there is no water or oil or wetness on it, fast will not be broken if the rubber coil is taken out of vagina.
(3-4) Fast will not be broken.
(5) In this case, fast will be broken, this is alike putting medicine into the vagina. Rubber coil is also inserted for the purpose of medicine and treatment.
Allah (Subhana Wa Ta’ala) knows Best
Darul Ifta,
Darul Uloom Deoband