First of all let me start by saying that your son is adorable. As for your hair, I would suggest to wear your hair down, or half up. If your hair is down it will lengthen your face, rather than pulling it back or up, which will make your face appear more round. If you pull your hair half up naturally it will give a soft romantic look and keep your hair out of your face.
If you are getting your make-up done professionally your make-up artist will take care of you. Just inform her about the problems you have with make-up and your uneven skin tone. As for the warm whether, if you are concerned about your skin looking oily you should use a mattifying lotion. This can be applied under or over your foundation. Also look into oil blotting paper. If you use them, just add powder for you face to look fresh, and prevent it from looking oily. For uneven skin tone it is best to add concealer under the eyes, and any major blemishes, and then add your foundation and powder.
Good luck,