Hi Sunstone
I have to say that I've been fairly happy with insurance companies when it comes to making claims on landlord's insurance.
The main stumbling block is that the claim can't be made until the "incident" is completed. So as all 3 of my claims have been people breaking leases/not paying rent, until that person has left, the unit has been cleaned and a new tenant installed, the incident is not complete. So that means it can be a few months of mortgage payments with no income before the insurance payment comes through. I believe that with a longer term claim (such as malicious damage where it may take months to get the property back to rentable condition) some companies will give you progress payments, but don't quote me on that!
Anyway, once my incidents are completed, it's usually taken 2-4 weeks for the insurance payment to come through.
I've never made the claims myself, the property managers have done them for me, and as far as I'm aware they've all been very straightforward. As long as all the required information is there, it's gone through very easily. And being good property managers, they know the process well and put all the right paperwork with the claim.
Hope that helps!