Istikhara is not obligatory in every marriage. It is helpful if you are unable to decide whether the proposal is good or not.
The Istikhara which you did is for your intention, while the Istikhara which the boy did was for his intention. You need to wait till any change in the circumstances takes place, then if you remain unable to decide and you still need an Istikhara, then both should go for one joint Istikhara.
Yes it is permissible for a woman to propose marriage to a suitable man. She can convey her proposal through a trusted person or through any suitable way like a letter or an email etc. Such proposal should be studied very carefully because it is not common among men, and it might be misunderstood or misused if the man is not pious enough. The man should be with high degree of faith, religious practice and manners.
As Muslims, we do not believe in caste, and we rather condemn such an attitude. Our criterion for evaluating someone is piety, as the Quran says. It is unfortunate that some parents still carry such a mentality, and hopefully one day we will all be able to implement our religion in the best way possible.
That being said, you must take into consideration compatibility and overall mindset of who it is you are marrying. There must be a good level of compatibility for you and your future spouse to have a successful marriage. It would be best for an elder or a local scholar to somehow discuss this topic with your parents, if you see this suitor to be appropriate for you to marry.
Do not allow this to escalate, or turn into major problems, and try to deal with it in a calm and wise way.
As for "love marriage", this is an unfamiliar term in Islam. For us, it is either marriage, or not. Love is one thing, and legitimacy of a relationship between two non-mahram people is another.
Although from a shar'i perspective this might not be obligatory, but one is asked it would be haram to lie and not tell the truth.
Also, ethically it is important for both sides to be transparent and clear about everything. Present everything to each other, and it is up to both sides to decide and agree, or disagree.
The problem with concealing such information is should it surface later on, it will become very difficult to contain and could lead to deep issues.
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