Sorry this is long winded.

Ok. So if it’s 25.00 or 100.00 what really matters is the value at the end of the day.
It’s pretty common knowledge that the Insurance or DRA or whatever is a profit center.
Unless you’re a Government entity your income needs to be greater than your expenses.
If company A lists a boat at 4000.00 a week and charges 25.00/day “insurance” = 4175.00
If company B lists a boat at 4000.00 a week and charges 100.00/day “insurance”= 4700.00
Difference on my calculator is 525.00 a week or 75.00 per day
I’ve chartered from A and that’s why I charter from B. I work hard for this time and the stress level is as close to 0 as you can make it. That’s where CYOA ROCKS
New or newer boats released at a rate of 5 or less with great customer concern or other companies on a slow day looks like they're starting a regatta.
If 525.00 or less difference makes or breaks it is your decision.