Originally posted by @Justin Seng:
When should you let an applicant know that you will require renters insurance? I already accepted a deposit to hold from my tenant and haven’t mentioned it. Is it ok to just put it in the lease and that be the first time they see it? Wouldn’t want to lose this tenant...
When I accept a tenant, I send them a "New Tenant Acceptance Letter" (usually via e-mail). It includes a deposit to hold agreement and any move-requirements (amount of deposit to hold and any terms or conditions associated with it, amount of move-in funds, utilities to be turned on in tenant's name, renter's insurance, etc). This is usually the first time I mention rental insurance and it has never been an issue. Of course, I've usually mentioned that they will get something from me with next steps required before lease signing if they are accepted. I don't think most tenants are surprised or bothered by this.
If you haven't yet, I'd suggest you read @Brendan Turner's book, "The Book on Managing Rental Properties". My acceptance letter is modeled off his. In general, it's a very useful book and can help you find answers to questions like these before they arise. There are other good books out there, but this is a pretty comprehensive one to start out with.: https://www.biggerpockets.com/store/managing-properties-physical.