Here is my experience.
Our insurance is through USAA. We have both automobile and homeowner's insurance through them.
On November 26, 2019 our wheelchair van was stolen with my Permobil F5 wheelchair in the van. Both were recovered a few days later.
I expected the automobile policy to cover the damage to the van, the damage to the wheelchair, and the contents of the van that were stolen and not recovered. It did not!
The automobile policy covered just the van and a couple of hundred dollars of contents. The wheelchair and the bulk of the van's contents were covered by my homeowner's policy.
Because the van was stolen, the incident was considered to be a "comprehensive" claim (rather than collision, for example). On our policy, there was no deductible for a "comprehensive" loss.
The wheelchair and the van's contents were covered by our homeowner's policy, for which there was a $1,000 deductible.
This arrangement may vary by state, but seemed to be pretty typical.
If you do face a loss, be prepared for the process to be long and drawn out. While our loss was over 9 months ago, I only received the replacement wheelchair last week (the wheelchair was damaged badly enough that it needed to be replaced).
Also, because our van was a wheelchair van, it was very expensive to repair. So expensive, that insurance decided to write it off. We bought the van back from insurance and had the necessary repairs made, but that took a long time as well (partly due to Covid 19).
After our van was recovered, we needed to do about $500 in emergency repairs to make it driveable. It needed thousands of dollars of other work that was done later. Because we could still drive it (after the emergency repairs), we only needed to rent a wheelchair van while ours was in the shop being repaired - a total of about 2 weeks.
Long before the theft, I had decided to add roadside assistance and rental reimbursement for the van to our auto policy. When I did so, I made sure the insurance company knew that it was a wheelchair van and the rental coverage needed to provide for a wheelchair van rental. They agreed. Fortunately, they recorded that phone call.
When the van was stolen, we reminded them of our need to be reimbursed for the cost of renting a wheelchair van. They initially said they would only reimburse us for the cost of a regular van ("large SUV"). I reminded them of the conversation we had years previously. They initiated a review, found the tapes of the initial conversation, and agreed to reimburse us for the cost of the rental wheelchair van.
For our part, we made sure that we only rented the wheelchair van when it was absolutely necessary.
While the whole process was a bit of a hassle, I give USAA very high marks for how they handled our case. In the end, they wound up paying around $60,000 for the claim. I am sure glad we had the insurance we did.
That claim is still not finished, but we now see the light at the end of the tunnel (or is it a train? we will know soon

).
Steve