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No one is bound to follow the Istekhara of others even your parents because it was based on their intention not yours. You must always keep the respect of your parents and avoid hurting their feelings.

Wassalam.

Mehr (Mahr مهر) is the right of the woman and she is entitled to receive it as and when she wants. She can ask for it before wedding and she can postpone receiving it. Even if marriage dissolves before she receives her Mehr, she will be entitled to receive later on.

'Wassalam.

As far as the conditions of marriage, only virgin girl requires the approval of her father or paternal Durand father for her marriage. Man does not need approval from his father or mother in his marriage, but it is very important to keep the respect of your parents and avoid hurting their feelings. You as a man are entitled to decide your marriage, without causing any harm or disrespect to your parents. You should try your best to convince them and get their blessings.

Wassalam.

Bismihi ta'ala

Yes, whether the female is Muslim born or converted to Islam, he will still need to follow the correct shar'i and traditional Islamic custom of process of proposal and everything else. Involving family in the marriage proposal is extremely important, and so is seeking their blessings and happiness. 

And Allah knows best