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Congrats on the baseball family. Are you in college ball right now? Teams like to think that talent runs in the family so having a bro that went in the second round definitely increases your chances of getting drafted with a descent signing bonus. Please, for the love of baseball don't join forces with Scott Boras!
Back to the trip, since the personal trainer is for an actual career purpose (not just to look good for the ladies) don't screw him over. He could be an integral part in making it. Do you have a credit card? If you do, charge it and pay it off $20/month till you can afford to take care of it all. How far away is the trip? If you have enough time you might be able to apply for one and use it to get you there.
I know a lot of people say to not charge fun but this is sort of a once in a lifetime deal?
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