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It's difficult to guess what kinds of problems you are having, so I offer this a merely one possibility for you to consider.
In this example I filled a type box with many repetitions of "we are the best", copied, clicked the outlined W with the Area Type Tool, and pasted. I decided on a type size that pleased me, then began to select each "we are the best", one at a time, and to adjust the tracking in the Character panel to make the phrase fit the space. Click in the Tracking number field to use
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Not quite sure what you're after. Is one of these even close?
Thanks,
Peter
It's difficult to guess what kinds of problems you are having, so I offer this a merely one possibility for you to consider.
In this example I filled a type box with many repetitions of "we are the best", copied, clicked the outlined W with the Area Type Tool, and pasted. I decided on a type size that pleased me, then began to select each "we are the best", one at a time, and to adjust the tracking in the Character panel to make the phrase fit the space. Click in the Tracking number field to use the arrow keys to increase or decrease the spacing as needed. Obviously, I didn't finish the process. Yes, this is tedious and long, and I know of no way to do the whole thing in a click or two. There are several to try to make words fit: you can change type size, stretch words vertically or horizontally, change fonts, add strokes, offset path, etc., and my choices will be different from yours. I hope this will be of some use to you.
I'll be starting on this project later today finally, so I'm very hopeful that your instructions help me accomplish what I'm hoping to.
Thank you so much for your time and willingness to help 
I had to put this project off even longer to complete others, so today I'm diving in and here is the first issue I run into. See attachment.
For context: I'm opening a EPS vector file with the company's name spelled out, and I want to type their slogan over and over inside each letter as mentioned before, then removing the outline.
In this photo, I had just typed on the H to begin typing with the area type tool. And this is the popup I got right away. As always, very thankful for any time and help you're willing to give as I'ma complete AI noob.
Yes - I was selecting the stroke, not the inside of the letter. It says path beside my cursor when I hover over the black outline of the H - see attached image. (As always - THANK YOU PETER) 
I don't believe you need to start from scratch, Tiffany. What you should do is go to the Layers panel and click the reveal icon
in the red circle and see which, if any or all, of the letter shapes are compound paths. If they are, you need to release them, because you cannot convert a compound path to Area Type. ⌘+⇧+⌥+8 Mac or ctrl+ shift+alt+8 Win or menu Object > Compound Path > Release.
The letter A is a special case because of the counter, or hole. Ordinarily, in outlined type, the two paths forming the letter would be compounded to form the opening in the fill of the outside path, but a) your paths have no fill, and b) you can't use a compound path.
A solution is Object > Text Wrap > Make. In all likelihood, you will want to go back to Object > Text Wrap > Text Wrap Options, and set the Offset to 0.
Please let me know whether any this helps or only confuses.
Peter
I did what you said and I believe all letters have been released now. I attached a screenshot so you can see what I see over in the layers menu.
Does this mean I can likely follow the instructional video and the instructions you've outlined in this thread now without interference?
Is there anything I need to do once I complete the text within each letter in order to "unrelease" things again, or?
You have just been a WORLD of help to me. Thank you, thank you, thank you.
x Tiffany
Okay, I'm having success! I completed one letter - the H. This was pretty easy. Peter - the advice you gave me on going into layers and releasing made the YouTube video successful and I was able to follow the tutorial.
I think for the next letter A, I want to put an image into the character. I'm confused now on how to clear out that middle section of the A, though...
What do you suppose I'm doing wrong? This is what I got from following your first step:
Would making a clipping mask be easier? Would it be alright if the letterforms are cut off along the larger letters' edges like the example here?
I'm happy to go this route, too, just to give my client a couple of options to choose from. If you have time to explain how you accomplished this, I'm certainly all ears (eyes in this case) 
Thanks Jake!
- Create the text that will be contained within the larger letterforms.
- Create the larger letterform and place it above the text.
- With the larger letterform selected, Go to Type -> Create Outline -- (this will convert the type into a letterform shape like you had done before)
- Select both the text and the now outlined letterform and right click to bring up the drop-down menu, then select "Make Clipping Mask"
- this will make the letterform shape a clipping mask to the text that is behind it.
If you need to move or change the text inside the clipping mask, just double-click on the shape. You will see the "<Clip Group>" selected in the upper ribbon of the document window. Double-click away from the shape to go back to the regular artwork.
I use this technique all the time for a number of things. Hope this helps you.
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