It is very rare that I find a woman that I would consider dating. I'm 23 and only been in 1 relationship. It seems however that everytime I DO find what seems to be the one for me, there's always a big obstacle obstructing my path. How does it always work against me like this?
Because no one is perfect, and relationships are not "found", they are BUILT.
Everyone has baggage or issues. You need to determine what is worth working through and what the deal breakers are... PLUS, you are pretty young, so it's not likely you will find many women at a place in life where they are relationship material.
It gets better in your later 20's/early 30's. People are more stable in life financially. They usually have a steady job at that point and are finished with school. They know who they are and what they want in life.
At the end of the day, perfect women/relationships don't manifest on their own. YOU have to put in the effort to create and build the type of relationship you want, and be the type of person you would want to be in a relationship with.
If you believe in god you could say that he hates you (cop out way) but it seems to me that because you seem to find several "perfect girls for you" that maybe they aren't in fact your ms right. I don't know but don't give up ok😊