Were you in a relationship over the summer, or just friends?
How does he feel about you coming down?
The last thing you want to do is not go, and then always wonder "what if" It sounds like you and he had a good connection, and while a long distance relationship isn't easy.....it isn't impossible either. Since he wants to come up in the winter this tells me that he is indeed interested.
As long as you go when he is not busy with baseball, then I see no reason why you can not go. Though keep in mind what ever you do there are no guarantees that things are going to work out, so it may be easier for you to sit back and wait until the winter when he can come out and save yourself from spending all that money.
In the end I can not tell you what to do, only you know what is best for you. If going is going to make life harder for you by not having money then I would say not to go.....but if it would not harm you then go ahead and have some fun! At least you will never have to wonder "what if"