A buddy in his 60's didn't renew the insurance on a bunch of toys (ATV's, boat etc) due to an illness in the family. When he went to renew after four years his insurer wouldn't talk to him without him putting a sack of gold on the table. Another agent basically told him that if he packaged everything, house, cottage, several vehicles etc it would get things going. I don't know if he's resolved the situation yet.
I guess it can vary depending on each case. I got another quote for 1k/year once I bundled with a car, of course that will likely be the one that I go with. Has he tried asking other companies? Is it his previous insurer that is denying him coverage now?