In the context of marriage, istikharah should only occur if someone is two-minded about two different proposals at once, both being equal.
For marriage, you should do a background check on the person, research about them, look at compatibility, try to understand who they are, their family especially, and then consult with well-informed or experienced people.
How actually religious are they? How is their akhlaq and what are their moral standards? These are the two primary questions you must have an answer to as well.
It's only after this that you evaluate the situation, and see whether or not you are still confused and two-minded, in which case you can do istikharah.
Faal is different to istikharah. Faal is trying to find out what will happen, whereas istikhara is is about whether you should go ahead or not.
In any case, these stages should be pursued, and if you are convinced, and done all your required work, you do not need to resort to istikharah.
If you already made the decision, there is no point to taking istikhara.
Anyway, it is good to talk with your mother about her concerns since she probably has some solid reasons for her view.
However, if you really don't like medicine, there is no purpose in studying it, because we don't do well at things we don't like. Also, no one wants to go to a doctor, nurse, surgeon, pharmacist, etc, who is not 100% committed to their job.
Wishing you the best, whatever you do! (And this answer is probably late!)
Istikhara should not be done again unless the situation of the matter has changed. If there is no change in the matter, there is no points in trying to do an istikhara again.
Istikhara can not be repeated if it comes against what we mant. The only situation in which another Istikhara can be repeated is when the total situation changes and it becomes another matter.
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