In most mangas, the guy usually has past issues or say, for instance, he's a host or player and that just ruins the relationship. Well I want this except I want the girl to have the issues or be a hostess or a member in something bad that negatively affects a relationship. Romance can prevail or not doesn't matter to me Thanks!

Okay, so all the ones where the girl is something bad... it doesn't really affect the relationship poorly, haha. ^^ Or anyways, all the ones I can think of maybe aren't dark enough for you? But I think they work.

Gokusen <- where the girl is a yakuza leader
Monkey High <- I hesitate because I didn't like this... after a while there was no plot except for "CANS I SLEEP WITH YOU NOW PLZ," but the first half fits your description to a tee
Matsuri Special <- not sure, but her job and abilities are a huge problem for the guy she likes
Ojousama no Himitsu <- the last two stories, and with a twist

What about Maid-sama? Haha. I think I'll watch this thread- this topic interests me and I might pick up some suggestions, too.

Delivery

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Emma - Shes a maid and hes an aristocrat. In this time period having relations with someone outside of your class, especially marriage, was frowned upon or considered deviant behavior.

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Feed your head.