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You could try vinyl plugs that can be found in hardware/home improvement stores. The plugs come in various diameters. If there isn't one for the hole's size, you may have to drill it larger to the size of the plug so that it will fit. Also found this kit, may be this will be an alternative option.

Unfortunately, you NEED to remove or cover the old vinyl. If you attempt to tile over an unsecure base, you are wasting yout time and money because the tile will not stay down. In your case, if you go over the splitting vinyl, the vinyl will continue to separate and up will come the tiles. If you go over the paper layer, the mortar/quickset will not stick ...

Make a 4" dia plug from a 1x6 or plywood, screw eyelet into center, clamp plug into dryer vent with worm gear clamp. Pull through with your fish tape. Perhaps a taped cone could be centered over the plug (and the fish tape lead through the center, for better insulation tracking). Down the road this lint brush will remove any buildup. This one has a 10ft ...

You will certainly need to provide for some drainage of the now "lower" track of the window so that accumulated water can flow out. One thing to also consider is the overall design of the window itself. Many window units are designed with a definite UP and DOWN side to them. When you rotate such window by 90 degrees certain aspects of the window may be ...