Agreed. You alaways have to look at the details of the particular situation. In general however, the people that underwrite insurance policies are pretty good at what they do, and they are going to set the premium to take a $5,000 deductible down to a $1,000 deductible at a price where they make money.

So you start with the presumption that buying more coverage (i.e. lower deductibles) costs more than you'll get out of it.

That said, I'm involved with the insurance buy for our company, and our Self Funded Retention (essentially a deductible ) fluctuates in arange from $250,000 to $2,000,000 each renewal depending on how hard or soft the insurance market is that year.