Regardless of the exact amount of slack, I would replace the chain while there - and probably the gears too. Cheap insurance.
Resealing the cover is going to be an "interesting" experience. I had zero luck with the thin paper gasket made by Felpro (and others). Just a bit of distortion on the mating faces, and it won't get compressed at all. Ended using a metal gasket (hard to find) and RTV on both its faces. The bolts may need re-torquing after they settle.
Whatever method you are using to seal the bottom to the oil pan, be very methodical, or it will leak oil from there.
The dowels have a bit of taper at the end, but nevertheless will fight you when trying to reinstall. Some just got rid of them. I used the two bottom cover bolts to (very gently) pull the cover over them.
You will need to block the crank from turning when torquing the bolt. Strap wrenches don't work. Some use a screwdriver stuck in the flex plate teeth - which I find a bit crude. I attached a steel bar to the pulley (using the threaded pulling holes) and supported it over the frame.
Good Luck!