Unix how to copy file to directory and echo

Your for loop only results in one item and this is then not used in your cp command. It could look like this:

BACKUP_DIR="/Users/ashleyschumann/BACKUP_FILES2/"
for item in /Users/ashleyschumann/Pictures/*
do
    cp -r $item ./BACKUP_FILES2
    echo "$item copied to $BACKUP_DIR"
done

But as muru already stated cp -v will do this.

The easiest would be to enable verbose mode on the copy command

cp -av Pictures BACKUP_FILES2/

Or

rsync -av Pictures BACKUP_FILES2/

If you want to customise the message you need to iterate across the files. Since you haven't told us whether or not Pictures contains directories of files, I'm going to provide some alternative solutions.

First, a single level directory of files

#!/bin/bash
# Backup files from a single level directory
target=BACKUP_FILES2/Pictures

# ensure target exists
mkdir -p "$target"

# here we go
for pic in Pictures/*
do
    if [[ -f "$pic" ]]
    then
        # it's a file
        cp -p "$pic" "$target/" &&
            echo "Copied $pic" >&2
    fi
done

Next a couple of options for a directory tree of files.

#!/bin/bash
# Backup a tree of files using cp and a customised message
target=BACKUP_FILES2

find Pictures -exec bash -c '
    for i in "$@"
    do
        if [[ -d "$i" ]]
        then
            mkdir -p "/tmp/target/$i" && echo "Created directory $i" >&2
        else
            cp -p "$i" /tmp/target/"$i" && echo "Copied $i" >&2
        fi
    done
' _ {} +

Or

#!/bin/bash
# Backup a tree of files using rsync and a customised message
target=BACKUP_FILES2

find Pictures -type f -exec bash -c '
    for i in "$@"
    do
        rsync -aqR --no-r "$i" "$target" && echo "Copied $i" >&2
    done
' _ {} +