Sounds like it's going to be first time out for a couple of people..
Assuming that the tires the car has on it now will pass tech (tread depth, overall condition), he should just drive the car the way he's familiar with it being. If the tires need replacement, I think staying with 245/50's would be the way to go. That way he gets to use them in his DD without any downsides. If he gets hooked, he's going to want to step up well past 255's and 18x8.5's.
Side note - most track day organizations require a roll bar in order to track a convertible, and it will probably have to meet some spec.
Norm
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'08 GT coupe 5M (the occasional track toy)
'19 WRX 6M (the family sedan . . . seriously)
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