First of all, living out of town & having BH married off all of my children, I feel that I can comment on this.
I think the question on the table is not the cultural differences between and out of towner & an in towner, because many a time that is not even check into just because the girl is an out of towner. The question is whether a boy should go out of town for a date. For this we have a Mekor in Chumash. Avraham sent Eliezer out of town to look for a wife for Yitzchak & Yaakov was sent out of town to find his Shidduch. So what is wrong with looking out of town. As far as the travel goes, many a bochur do not hesitate to run out of town for their friends Lchaim of wedding. It is not Bitul Torah then?
If a boy wants his wife to support him, (or her parents) why doesn’t the boy have the Derech Eretz to meet the parents when he picks up the girl for the first date? Why is it acceptable for the girl to leave her (paying) job, lower her level of Tznius (to run after the boy )and go to where he is.
My boys traveled for the first date to where the girl was, & I was Makpid that the boy came to my home before I let my daughters go out with them. It was just one of the criteria that I based my choices on. ( & not the color of the tablecloth, what type of dinnerwear they use on Shabbos or many other non important things that people check into before allowing their kids to date)
May Hashem send you the proper guidance with this whole inyan, and may you find your Zivvug soon.