Dating is always a little bit more complicated when a couple lives in two different cities where there is a commute that's longer than an hour or two. Even one or two dates can get complicated, and that potentially increases by dates three through whenever things start getting a little more serious (and the couple can work out kinks by communicating directly).
It's a smart practice to set up a date with a potential time for the next date. Because one person or the other will likely be traveling to the other's city, it makes sense to try to get in more than one date at a time. This doesn't mean that either party is committing to two (or more) dates at a time, but rather saying that if this date goes well and we want to go out again, such-and-such would be a good time. They can just as easily decide not to go out again and forget about the fact that they already arranged a potential time for another date.
In the same vein, it's important to get back to the shadchan (or each other) in a timely manner after each date, as perhaps the couple can get in another date before the one who traveled in returns home. Or, travel plans will need to be set up for the next date and advance notice is always helpful with that.
Because it is likely that there will be more time in between dates when there is traveling involved, keep in mind that momentum is crucial in a shidduch. Often couples will not be communicating between (beginning) dates, so they can lose familiarity and comfort if too much time elapses between when they speak to each other. They don't want to have to start all over again each date. Phone and skype dates can be helpful to bridge that gap, but be careful with them, because they have their own potential pitfalls.
One person should not expect either person to do all the traveling. Sharing the commuting is the most mentchlach way to go about it. Meeting up halfway can work well too when the distance is only a few hours by car. Websites like whatshalfway.com and meetways.com can help you find venues almost exactly midway between your two locations.
Sending your date home (if s/he is traveling) with a care package is thoughtful and sweet, but be careful not to string someone along if you don't plan on continuing things. Similarly, think about what you're up to relationship-wise before you ask someone to text you when they arrive home safely.
There is a school of thought regarding treating long distance dating like local dating in terms of speaking with/hearing back from the shadchan and deciding whether or not you would like to see your date again. It can create undue pressure for either party if s/he feels like s/he has to make decisions really quickly or must continue dating someone because s/he is already in his/her city. On the flip-side, the couple may decide not to go out again because there is traveling involved, but if they were in the same city, they would likely have gone out again. It complicates things less if the traveling is not considered as part of the "Do I Want To See This Person Again?" dilemma.
All the aforementioned speak to a sampling of practical issues involved with dating someone who currently resides somewhere outside of your immediate vicinity, but keep in mind as well that sometimes there are cultural gaps and the like when a couple come from different geographical backgrounds.
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