I would preferr the other style installer. with this one you posted above there is too much of a chance that you leave it loose and or rotate the rivnut while in the hole as it's compressing.
as for the sealer I wouldn't use any rubber washer as it might cause the insert to protrude further out on the top side making it stick up too much. how hard is it to pull some trim back enough so you can get you hand up into the headliner and oose some RTV on the bottom side along with maybe even putting a nord-lock washer onto the back side before you compress it so once it's compressed it will have more "grip" on the sheet metal. the ridges on the nord lock or ribbed lock washer will grab the sheet metal along with the ribs on the rivnut to give a tight hold.
This is the style tool I like. there is no chance of rotating the rivnut while compressing it.
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