Same procedure as all vehicles. Start with bleeding the right rear then left rear then right front then left front keeping the reservoir full at all times.
Cutlass S, yes Cutlass or Cutlass Supreme, no Interwebs search of photos will show the difference- the raised center section. Oh, for details, the 442 will NOT have the "Oldsmobile" script (or holes for it) in the left front corner.
I have a 1969 Oldsmobile Cutlass supreme. My car has a 1968 front bumper, hood, and grill. Its mirror of your question but If a 68 can go on a 69 I wouldn't see why a 69 couldn't go on a 68.
Here are links to a 1968 Olds Cutlass chassis wiring diagram http://i168.photobucket.com/albums/u169/mitsu-dave/Oldsmobile/8ef65d8d.jpg?t=1219880010 http://i168.photobucket.com/albums/u169/mitsu-dave/Oldsmobile/5d8d79ca.jpg?t=1219880045
22s with 255-30-22 tires you neeed to get longer lug studs and this is the biggest ive gone with out having to cut or lift done it on my 68 and 72 cutlass
All 1968 Cutlass two doors had Chrome Louvers on the hood. All others did not. The Hurst/Olds had painted louvers. http://www.who-sells-it.com/cy/brothers-automotive-products-4264/oldsmobile-cutlass-442-parts-fall-2009-20699/page-22.html has the part if you need it.
No it will not fit correctly with the grill.
68-72 Oldsmobile big block 455
push in turn to the left and pull out
68, 69, 70, coronets, or chargers disc brakes will fit.
Compared to todays modern brake systems they will feel hard. Also depends on if they are power brakes or not. Some cars of that era did not have power brakes and they were very hard to push.
hurst shiftersthe hurst shifter was an option in the 68 thru 72 Oldsmobile cutlasses.
I don't know how many were made but I would say they are pretty rare as I worked for a dodge dealer in 68 and only remember seeing 1 R/T that came in that had the disc brakes on it.