The shipping would most probably match the price of the guitar, assuming that the seller would want to ship to you in the first place, remember that there is a higher chance that overseas buyers may be scammers, so he also you have his precautions.
Also, vintage guitars may not actually be that great players, but still hold it's value for the sake of collection. After a few decades, the condition may not exactly be that great and there are problems that can be avoided using clever positioning of photos and euphemisms. eg. frets may be worn down and require refretting and he states "frets not exactly in mint condition" photos can barely show the fret condition unless special attention is given to that. And also, the temperature and humidity change can very well warp the neck. I suggest that you play the guitar, especially if it's old or "vintage" to see first hand how you like the feel, and playability. Reviews may not always conform to your personal taste. For all you know you may hate the feel and sound of a 59' Les Paul. An advances in technology has allowed playability to be greatly improved, action lowered without that much buzzing etc in modern models, which may surpass that of "vintage" design.
Another thing is the probability and reputation of the seller. I wouldn't trust a seller with 10 feedback selling say, a pre-CBS 1950's strat, with his description: PRE CBS FENNDER(NT PRS GIBSON EPIPONE) START GOOD CONDTIION NR!!!!!!
And should you decide to penny pinch and use a cheap courier without insurance, and the guitar fails to arrive, you would kick yourself.