I recently complained about this issue, but was able to resolve it by using new cables. The problem lies with the use of any adapter with the cables. So by using a USB-C to HDMI cable for one monitor and a USB-C to DVI cable for my second monitor, it works perfectly. So now including my Surface Pro 7, I have 3 monitors to work with which is exactly what I was looking for. All 3 monitors turn on as soon as I dock my Surface Pro 7 and turn it on.
Remember, don't use any adapters with your cables (Anker or whatever other brand). Just use a single cables directly from the USB-C slot on the Dock 2 directly to whatever input your monitors may have - HDMI, DVI, USB-C, etc.
And there is no need to buy those $65 cables that Microsoft sells. You can get good cables from Amazon for a fraction of that price. Good luck!