If the crawl is vented insulate the duct if it is not vented insulate and condition the crawl.
the best way to insulate duct is to wrap it national building code calls for a min R5.7 I use 2" fiberglass batts they come 47" wide and 50' long roll you can get other sizes but that is the standard.
Begin buy sealing all the connections with mastic or mastic tape code calls for 181 tape but you can get the same product without the label cheaper. Do not use duct tape or silicone as these will not stick.
Pre cut your insulation take the total top + sides + bottom then add 6 " for an overlap.
You will need to buy a stitcher (Aro p32 stapler) wrap the duct cutting around the takeoffs lapp to the corner and fold 2" under so you can stich the foil wrap together. Now tape the ends all the way around the duct.
This is an excelent diy project as it requiers time and lots of it but no particular danger of doing it wrong. Also you can save a butt load over having my crew do it. A recent job: 3' crawl wraped 50' of trunk and 200' of branch. Took 3 days $200 in matterial. Job cost $2,700 so if you can crawle around and do it you can save $$$
This is a two man job you really need one man on each side of the duct.
If you do not seal the duct you will endup with a balloon