Keypad and Remote wont work together

So we just bought a house and it has an older model Craftsman opener. Works just fine using the wall button inside garage. Previous owner left us a remote that doesn't work and theres an exterior keypad with no code provided. I replaced the batteries in BOTH and began to program them using the simple process of holding the “learn” button to clear all previous codes prior to syncing.

I begin by syncing the keypad and creating a new code. Simple enough, its working great in under a minute. Now I move on to syncing the remote. Another easy process that is done in less than a minute and now the remote works great! Unfortunately, the exterior keypad no longer works! What the?!? So I proceed to reprogram the keypad and now that works great....but the remote doesnt work now?

Bottom line: I can “learn” the remote OR the keypad but they wont work at the same time. One works and the other one stops and vice-versa. Im not clearing the codes every time I sync by holding the “learn” button too long until the bulb blinks/clicks. Im just using a simple push to light up the tiny LED thats next to the button. What am I doing wrong?