I am going to assume for question 1 you are referring to the work orders list screen and question 2 you are referring to report designer.
1. I'm not sure why its only entering 14 days apart. Did you customize the screen? Try using the stock one and see if it is still doing it for you. When I tried the stock screen it doesn't seem to occur.
2. Have you already tried the stock reports work field services? I believe they might work for you in this situation.