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For me it's simple - if the car turns out to be shit, can you take the financial hit of offloading the car without it bothering you or affecting you financially in a major way? If yes, go for it, if you've done all the vetting you can without seeing it in person. If not, you simply have to eat the cost of a flight out.
Also, it's critical when buying a car out of state to make sure that dealership has a good reputation for handling such transactions. If they treat you like any old buyer, it will NOT go well. If you end up getting it shipped - the same applies. A random dealer will not know how to handle this properly and it will leave you frustrated.
I got lucky and bought my car sight unseen from a state over. This is a relatively well known dealer for high end cars and the car was flawless. In addition, they rolled out the red carpet for me. This is the type of dealership you want to have in these cases.
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