we apply work permit for nanny via MOM. Takes about 2 weeks to process. Some of my friends do not apply insurance for nanny but we do, just in case. Apply from any 1 insurance agencies. I forgot how much is the cost as it was quite long ago. I think most importantly you need to bring nanny for medical checkup for illnesses or diseases like TB etc so she don't pass them to your child. when you hire a confinement nanny, you must pay for her medical expenses (be it external nanny or agency nanny).