If one can’t figure out for themselves who and when either one of them should travel, then why accept dates from out of the area? If that is going to be an issue for the first date it is going to be an issue for the rest of their lives. Where they will live, when to go to which set of parents for Yomim Tovim, when to visit, who will pay for the visit, etc. If the date is within driving distance there is no reason why the boy should not go. If however it is truly long distance, that is something the shadchan should know before she presents the shidchuch. Many young people plan on being “in town” for a week or two of dating to make things go more smoothly, unfortunately when this happens shadchanim tend to set them up with more than one prospect.
How wonderful it would be if people would not go looking outside their own daled amos for their zivig but truly evaluate who’s right next door. I guess they believe things are always greener on the other side.