I mean I can live with it even though sometimes its over the top.
There is a big difference between living with something and thriving. Be honest with yourself about how you really feel about this. It isn't easy. Is this something that you want to draw a line in the sand over or is it a minor annoyance that doesn't really have that much impact on you.
I guess I would rather him be sending them to me than someone else... .which I am certain he would do if I asked him to stop. He would use it as an excuse in his own head to cheat.
IF you were to take this out of the equation, what would you do? If you could ask him to stop without worrying about him sending them to somebody else, would you ask him to stop? It is so difficult to make decisions based on how I honestly feel rather than making a decision out of fear of my husband's reaction. You are in a FOG state and that makes it really difficult to see straight and figure things out. A whole lot of us have been there or are still there to one degree or another.
Is it unhealthy to not make this a boundary? (Unhealthy of me and/or him?) (I guess I am asking if I am crazy for allowing it? I question my own judgement with everything now)
You are not crazy. You have identified an issue that bothers you and now you are trying to seek input to make an informed and rational decision about how to deal with it. That is not crazy. That is actually pretty level headed. Everybody is different. If you like getting an occasional picture, then what is the problem? There is only a problem IF you don't like it yet allow it to continue. It is only unhealthy to not make the boundary if it is something that truly bothers you. Like Crumbling said, there are more options than letting him send you pictures all the time or asking him to send none at all.
Some other things to consider:
-Does he expect you to respond to every picture he sends? If so, do you? If you stopped responding, would he stop sending them?
-Is it possible to quietly delete the pictures without looking at them?
-Do the pictures interfere with something that you are doing?
It really helps to look at YOUR situation. People here can ask you questions and share opinions and give you food for thought. Ultimately, it is up to you to decide what will realistically work for you.