Hi
Going back to your original problem...
If you have images that are AR 10:6.65 they are not obviously 16:9 and will therefore display areas on each side that are chequered ...

These will be transparent if the image is used on a higher track with clips below. (On Track 1 the chequered areas will be black and export black)
If you Crop the image to 16:9 it will become smaller as you are Cropping it. Some of the image will be lost but what is left will have the 16:9 AR. The original crop frame will automatically be sized to fit the nearest sides of the image being used. In this case it will be fitted from side to side leaving an area at the top and bottom trimmed off. Now what you will see are the transparent sides just as before (The 16:9 frame fitted to the sides so nothing changed horizontally) but the top and bottom will now also be transparent as those areas have been cropped....

You can resize the Crop frame keeping the 16:9 setting and move it about but all you will achieve is a smaller cropped area with a wider transparent border...

If you wish to retain a full frame 16:9 image of your clip/image use the Zoom effect set with AR 16:9. This will enable you to effectively crop to a selected area. Set the zoom rectangle to outline exactly the area required and VP will then enlarge this to fill the frame correctly and there will be no black borders.....

Between 10:6.65 and 16:9 you will lose very little of your image. If everything else is 16:9 (usual videoclips) just export in the file type required (avi/mp4 etc) but setting the chosen 16:9 resolution values (1280 x 720...1920 x 1080 etc)
Nat