I want to be able to load/download a bunch of resources and notify the user of the file that's currently being loaded, but I can't just draw a frame after each file starts loading because v-sync will wait until it can draw a frame before it continues (bottle-necking the loads to less than 60/second).
Is there a way to check whether the device is ready to draw or not (without hacky "has 1/60th of a second passed yet?), so I can perform actions until it's ready? I don't mind if the notification skips over files that finished before it's ready to draw, but I want to maximize the speed of the loads while still being able to notify the user.
Also, I'd like to avoid disabling v-sync even temporarily because I don't want to cause a graphic card crippling 300FPS rate if the computer loads really quickly.
You don't specify which version of Direct3D you're using. With D3D9 you can pass D3DPRESENT_DONOTWAIT to your Present() call and it will return D3DERR_WASSTILLDRAWING if the hardware is busy processing or waiting for a vertical sync interval. This means if you have vsync enabled, in your main loop you can just call Present with the DONOTWAIT flag whenever you've loaded a file and load another if it returns WASSTILLDRAWING. 
Note that you need to get the swap chain and call Present() on the swap chain rather than calling Present() directly on the device to be able to pass this flag to present, or you can set it in the D3DPRESENT_PARAMETERS structure when you create the device or create an IDirect3DDevice9Ex instead of an IDirect3DDevice9 device and call PresentEx() instead of Present().
This doesn't solve the problem of files that take longer than a frame to load however - your frame rate will drop if you have a file that takes a long time to process. A better solution to this problem in my opinion would be to move as much of your IO as possible to another thread (in D3D9 you will still have to create D3D resources on your main thread however) and just pass the name of the file that's currently being processed to your main / render thread to display each time you present a frame.
How can I perform actions while waiting for vertical sync?