The problem now is that the gambling site is, demanding for a wagering requirement this make me hesitant to proceed with meeting the wager requirements because of the fear of losing everything.
First of all:
[1]. May I know what brand of casino you use, do they operate on Bitcointalk, if the casino advertises here of course they have a representative here who handles your problems and can help you, plus proof of delivery, support can be tried as usualthey have from charging problems like that.
[2]. And if they have to require every user to play when the deposit comes in, try playing in small amounts first, at least you pass their requirements, for example you can bet $2 or $5 in any game.
[3]. Different online casinos have different deposit requirements, in my experience excessive deposits can be transferred back whether you play or not.
Because the casino you deposit has playing conditions, yes, maybe you can take point (2), I think so.