What's the total impact of the two schedule changes? If it's 30 minutes outbound and 35 inbound, you're unlikely to get sympathy. Similarly, if the first flight is changed by 30 minutes and the second by 35 minutes in the same direction, you have five more minutes for the connection and will arrive 35 minutes later than originally planned, which won't allow you to change to totally different flights that normally would cost more miles.

However, I'm confused since as a DM you are not subject to any change fees on award tickets. You can change flights as many times as you want up to T-72 as long as award space is available at the same cost (low/medium/high) in miles.