over the past year, my stock keyless entry started acting up. At first it just didn't want to lock any long, but it would unlock. I starting manually locking the doors before I exited. A few months later that started to fail as well. Now when I leave the car I have to push the lock button 3 or 4 times to get it to activate. The keyless still unlocks but never locks now. Suggestions on where to start?

 

I haven't tackled this myself, but if you hear the actuators trying to work the locks I had read that you need to grease the locking mechanisms.

 

Broken wires in the door loom.

 

Both.

Use a good penetrating oil on the lock mechanism. That will dissolve all the hardened gunk in there. Once it's moving freely, follow up with white lithium grease.

 

Sounds like it could be a couple of things. The lock actuator motors are not serviceable. If you hear the actuator when you press the lock/unlock then the gear inside the actuator is probably done. It's not too hard to get to them. The door will have a couple of screws. Remove those and then start pulling the panel off around the edge. There are 10-12 little plastic cones that hold it in place. Pull slowly and they should not break. Using a trim removal tool will allow you to get further in and get right next to the plastic pieces. Otherwise, get one part started and get your fingers in as far as possible and work your way around. Remove the rods to the door lock mechanism and then unclip the wiring. The panel will then pop off straight up. It sits in a channel inside of the window. You can remove the whole assembly and clean it and then relube it.
I have a couple of bad actuators that I need to cut apart to see what goes bad inside of them. I picked up several at the local pick a part and replaced mine with those.
With your description, it sounds like it may be the wiring connector. I have the same problem if I don't press the connector all the way in when replacing the door panel. Regardless, sounds like you'll want to get the door panel off and have a look inside to get it working right.