Short answer
I wouldn't. These policies aren't guaranteed to exist in the future, and the insurance company can end the offer at any time, usually without advance notice. If you already have the policy, they can't take it away from you. If you don't, you may not be eligible anymore.
A short clip from his webinar for residents and fellows, with captions.
Watch the full webinar from 30:06"I'll just get it right before I graduate"
A lot of people come to me and say, okay, this sounds great, let me wait until a month or two before I graduate and I'll get the GSI policy then. I want to be very clear. These policies are not guaranteed to be in existence in the future. The insurance company can terminate these offerings at any point in time.
Why offers end
The insurance companies closely monitor the metrics of these policies. If the metrics don't align with what the insurance company is comfortable with, they can and will terminate the offering. And they typically don't give advance notice before terminating these offers, because they don't want a fire sale on these types of policies. Insurance companies pull these offers all the time.
Once you have it, it's yours
If you already have the policy, they cannot take it away from you. But if you're banking that it's going to be available at a later date, you're simply rolling the dice. So I always suggest getting these policies sooner rather than later. Don't gamble and hope it's going to be available when you have a foot out the door from training. Lock it in now. You're not going to go broke, and you rule out the uncertainty.
Where Jay covers this
Jump to each moment in his webinars.