You may not want to share, but why did you need to send her money to begin with? Was this more of a my treat go relax or she is kind of financially dependent on you? This may change my opinion a little. If your wife doesn't work, it could lead to tge perception that you are controlling or insecure true or not.
As it stands, what you mentioned is not enough to speak to you being insecure or not. I get the strip club thing as long as the same applies to you.
I wouldn't put a club in the same lane but I understand the concern. The thing is women are targeted by men regardless of where they go. The alcohol adds more to something going bad, but the Mexican restaurant likely serves alcohol too. The thing ill say about women and clubs is they tend to interact with each other more than men. Your wife probably has a lifetime of navigating those types of situations. Your wife going to the club every blue moon is different than going every weekend.
Girls trip. Again, i get it. The lifestyle of a single woman is different from that of a wife. However, there maybe be legitimate things you are interested in that her friends are. For example, the way you party in front of your grandma isn't how you'll behave in front of your friends. A family vacation is going to be a different experience than you and your wife going alone. Unless you believe your wife's friends are fun girls/party girls, I wouldn't concern myself. I assume you choose your wife because she was respectful of herself, family and you. Going back to the strip club, i know how to enjoy myself while there and what is stepping over a line my girl may take issue with. I suspect it's the same for your wife regardless of her environment.
Like someone else said, i prefer my girl gives me space, so I don't give a fuck where she goes or with who. I trust she'll make the best decisions from safety to boundaries of our relationship. If something too off the wall happens, she won't be my girl and I assume the same thought is true for her. Im also not dating/marrying anyone who is easily influenced, so whatever she does it waa ultimately her decision.