Yes the rear brakes can be tricky or "simple"...
Perhaps, if you share where you are located, one of the many helpful people here on NAM stop by and lend a hand. I have experienced both types of rear brake issues (easy & fighting all the way), my advise is..
- when using the Harbor Freigh tool -which I do too - I found focusing more on twisting the pistion vs pressing the piston works better. If you press to hard it will bind up.
- If the piston is over extended - i.e. worn the pads down very low - the piston might have disengaged from the threads. Now the piston has to be "restarted" in the threads. You will need to press lightly and twist to get the threads to line up and start. Then see my guidance above.
If you are at step 2, it takes time to find the proper rotation on the piston to line up with the threads again and start twisting back into place. Imagine trying to start a nut on a fine threaded bolt - blind folded

. It can be done.. it just takes time.
Hope that helps.. Good Luck..