In other words, there isn't a guarantee? Also, how is health insurance handled since you mention COBRA? I was on another thread today where people were saying that health insurance is one reason they didn't take time off between jobs.
COBRA lets you continue your insurance plan from your employer for a time period after you leave.
However, your employer no longer contributes to the premiums, which are very difficult to personally front if you dont have an income.
You can buy temporary health insurance to cover yourself between jobs, but it typically is only useful for catastrophic injury, as the deductibles are extremely high to keep the price down.
Usually when I've been offered this arrangement (which I like because it reduces the risk on my side, too), the pay has been on the higher side for the contracting part, to cover the reduced benefits/security.
Given a choice, I'd recommend taking the contract period because if either party chooses to end the relationship, the candidate can honestly report it as a short term contract on their resume.
To a first approximation, no one is looking at employment gaps at that level of granularity. Now if you can't find a job for another year, that's maybe something different but you're back to switching jobs without really having a job.