The basic attempt to have a button prompt a standard system dialog box to select a file crashes on me only when selecting an image (PNG or JPG). I removed all filters and stripped logic to a simple SystemDialogInput call and the crash is repeatable. The interesting thing is that I can pretty much select through the displayed file chooser any other type of file (PDF, XML, TXT, NB,, JSON, etc.) ranging from few KB to GB in size as expected. It's only when selecting a PNG or JPG (didn't try GIF or other image formats) that the file chooser crashes and brings down Mathematica as well. After some time, I get a crash report with a "Reopen" button for Mathematica. I'm running v184.108.40.206 on Mac OS 10.13.2.
The "simple" line of code I'm attempting is:
Button["Image...", SystemDialogInput["FileOpen"], Method -> "Queued"]
I've also attached a sample JPG image I'm attempting to open although it seems any PNG or JPG causes the same behavior. From my observation, it appears when the file chooser tries to render a preview / thumbnail of the image, it brings down everything. I've also been able to narrow the crash down to only happen when the file chooser navigation is set to column view.
The steps to reproduce are:
I don't believe I'm doing anything wrong or out-of-the-ordinary here, but I'd be happy to learn otherwise. For the time being, I will change my settings to show files in list view (vs column view).
I got the same behavior in 11.2 -- it crashes.