My cropping workflow is a bit different from some, so this is how I do it. Others may completely differ, but there really isn't a right or wrong way to do things.
When I am doing a bridal, engagement, family, or infant session workflow, I always crop to the size the client photo is intended to be printed at. I didn't always do that, but clients got confused about cropping when I took a full size photo, and then cropped it for enlargements. Even when I explained to them that the photo would be cropped, they still assumed that the photo would look just like they saw it.
However, if I'm doing something like an event, a wedding, or a budoir that I know will end up in an album, or be purchased in many different sizes, I crop full sized. The way to do this is to open an image you took. Go to "Image Size", and it will tell you how large the image is. Put those numbers into your crop ratios. I often have several different cameras, and brands of cameras working on the same job, so I just average it. But if you are working a single camera job, then this should be easy. The important part of this is knowing when there is an "important" photo, one that might be purchased. You want to leave room in case you need an 8x10. (Digital cameras shoot in a 4x6 ratio, upgradeable).
If the camera doesn't shoot at a 16x20 straight out of camera, then you will need to upsize it. Many labs can do this for you.
Now: about Sam's Club, Costco, Walgreens, and soforth..........I will admit that all the equipment is basically the same. The difference between those place and a "good lab" is the paper the product is printed on, and the experience of the lab tech. If it's some 17 year old kid who is also a cashier, I don't want them trying to give me a print.
Two great companies for printing are MPIX, and Collages.Net. If you want to print your photos in your neighborhood, Wolf Camera is also good. They use great paper, and have pros manning the equipment. The cost is roughly the same. The quality is great. You don't want a good photo printed on a sub standard maintained machine, on crappy paper, when you can get a pro maintained machine on quality paper for a few pennies more. After all, it's your reputation.
Hope this post helps!
So to make things easier for the clients, who really don't understand crop ratios, I just made it the same crop they would recieve. It works out very well.