Aug 29 2017
I have a few videos I made using my Iphone 5s. I wanted to play them on my Ipad 2, about 3 years old.
Many of the replies here gave me hope but the details were a bit difficult to follow.
1. Place your videos on an easy to find folder. I placed three in a folder on the desktop. example IMG_0731
2. Start Itunes.
3. In the top left corner press the "Movies" box, Your purchased movies will appear on the screen alphabetically as usual. Note that I have the "Home video" category as my last item in the "Library" listing. Because I have already installed other home movies. See below.

4. Click on "File" and then "Add to Library" {Command+O}

This will bring up a window which will allow you to select the M4V files on your computer.
Here is what mine looked like.

5. Select all with {Command+A} or click on the first in the list then {Shift+click} on the last item.
6. After selecting them, click on the {Open} button in the bottom right of the box.
This creates the "Home Video" category you see above after item 3.
if you click on "Home Videos" you will see thumbnails in the window.
7. Plug in your Ipad and wait until it connects.
8. On the computer, click on the Ipad icon. Select the 4th item down, "Movies" to see your list of available movies.
Your home movies will now be mixed into that list.

9. See image IMG_0731 is among the other purchased movies.
10. select the home movies you want to upload to your ipad. And click on "Apply"
11. The movies will transfer onto the Ipad. A new category {"Home Movies"} will appear on the Ipad when you select the video button.
12. And just to make you wonder if you did something wrong, a warning window appears on your Ipad telling you "1 item could not be synced. See Itunes for more information" OK
13. This is your Ipad's way of saying it misses Steve Jobs. Just ignore the warning. It does not seem to effect anything.
...........Now you should be able to play home videos.
But it does not always work. Sigh.
All of my personal Iphone 5 movies easily loaded onto my Ipad but other m4v movies will not even upload into the computer in itunes. Including Apple tutorials and a purchased music video extra from Itunes.
I hope this helps. It was a challenge but worth it.