Wa alaykum al salam,
In my humble opinion, the best way to look at the situation is through a logical lens. You see, obstacles can be interpreted in opposing ways. So if for example you were going to a mosque and you find an obstacle blocking your way. You could probably assume that God is testing your will of wanting to go to pray. ie: will you find an alternative way to reach it or will you just give up. Arguably in this case the obstacle can be regarded as a test of will power. However, if for any reason one was on his way to a bar. And then God puts an obstacle in his way. Then one can probably assume that this is God giving a second chance for one to think about his actions. In this case it would be wise to back off.
What I am mean is, an obstacle, or lack thereof, is no indication on its own of whether one should proceed unto a matter or not. But only when these obstacles are placed on a foundation of logic (like the two examples above) could they infer a deeper meaning.
In your case, the best thing to do is to determine whether this women is a suitable match or not. And accordingly those obstacles could be interpreted as warning signs or as a test of persistence.
Hope this helps in a small way.
Regards,
Ahmad.