YES!!! I think you should make them!
Sorry, I don't mean to sound bossy! LOL I wasn't sure if I wanted to make them either, especially after I found 3 local stores that had really, really good sales on Disney tshirts & shorts for my son. BUT I ended up getting plain tshirts & started making them. I also got some shirts for myself.
If you look on my PTR, there's a post about the shirts. I got my shirts at Kohls & spent anywhere from $3-6 for them I think. My PTR has the exact prices of each. I then went to Hobby Lobby and found my son tshirts for $1.50 each! I thought they'd be crappy quality, but they are actually pretty heavy duty (so far anyway). They were originally $2.99 each but I got them 50% off. My shirts are mostly spaghetti strap or tanks but I picked up a few tshirts as well.
You can find plain tshirts at any craft store (Michaels, JoAnn Fabrics, Hobby Lobby, etc) and usually at stores like
Walmart, Kmart, Kohls, Target, etc. The craft stores usually have cheaper prices, but sometimes the quality is better at other stores.
I got my transfer papers from AmyMickey. I guess they aren't allowed to post the link on DIS because of the rules, but if you PM me, I can give you her website & contact info! I've used different brands of transfers over the years & I can tell you, I am sooo glad someone on DIS mentioned hers. They are the best I've ever used. You can also use each sheet more than 1 time which is really nice.
In addition to the tshirts, I also made my son a tote bag (his carry-on for on the plane) as well as some trip items for some friends of mine. Make sure you use the "cotton" setting even if the material isn't cotton. My tote bag was made of some type of thin material so I was afraid it would burn on the cotton setting, but the decal wouldn't transfer unless the iron was on "cotton". (just a little advice! I always learn the hard way! lol)
My son is only 2 years old & he gets excited whenever he sees me making the shirts! He says "Wow" or "oooh!" and smiles!

I also made them for friends of mine who have older children (ages 5-9) and they were all super excited to see their favorite Disney characters! And they were even more excited whenever I let them see the DISigns on the Internet & then let them help me print them & iron them on! It was great to include them in the process. I think it made them appreciate the shirts more than something I'd just pick up at the store! IMO, I actually like the DISigns I got on here better than what they have at the stores anyway...plus they are extra special since they are unique!!!
I would definitely make them! Its fun & the kids love them! Hope that helps!
After you mentioned your new bag on my PTR, I had to come & check it out!
I definitely like how the middle compartment zippers as well as the entire tote! I don't think a tote is weird for WDW, I just think you need to take whatever works best for you & your organization style! I'm planning to take my Vera tote with me as well, although I really like that yours zippers! As I said before, mine only has a toggle closure & I'm afraid of everything falling out everywhere. Good choice on the bag!