Thinkpad T500 Dual External Monitors Problem

Hi, i'm currently using this setup in Extended Desktop mode with the laptop closed:

Thinkpad T500, which has 1 VGA and 1 DisplayPort

External monitor (VGA)
External monitor (VGA to DisplayPort adapter)

Every morning, there's no rhyme or reason to getting this setup working correctly. I can start with the laptop off, both monitors plugged in, boot the laptop and get a completely different result each time. Connecting and disconnecting each monitor doesn't cause the changes you'd expect, and opening/closing the laptop functions similarly.

It typically finds a way to work after 5-10 minutes of random combinations, but never with the same method - sometimes I'll have to start with the VGA, open the laptop, plug in the DisplayPort, close the laptop. Sometimes, i'll have to do DisplayPort + Laptop monitor, close the laptop, plug in the VGA, switch the output mode to Extended Desktop (Digital Display + Monitor) and it'll work. The next morning, neither method will have any luck. Each monitor works fine individually. Any idea what's going on here? Recommended solutions?