Cushy, guided trips with shelters and prepared meals?

http://www.yosemitepark.com/lodging-dining.aspx

High Sierra Camps sounds like what you are looking for…guided, too if you want.

http://www.yosemitepark.com/Accomodations_HighSierraCamps.aspx

More direct link…note the lottery

Yep, that is what I saw. I just noticed though minimum age for children is 7 years old, bummer.

Does anyone know of anything else like this? Maybe to a lesser degree even? I understand this is kind of a one of a kind type deal. Are there any kind of guided trips in really cool areas anyone knows about where maybe they would handle the food even?

I'll carry all your gear, my professional chef buddy will do all the cooking, I'll even change diapers for the price of the High Sierra Camps.

Seriously now. Horse Packer trips will provide high levels of comfort and personal service without staying in developed camps. You can do traveling trips or base camp drops. There would be less horse traffic on the trails than on the trails to High Sierra Camps.

Dropping 200-300 pounds of gear about 10 miles from a trailhead, then picking it up the next week will run a bit over $1,000. Prices improve if the packer can combine your drop with another group.

Here's a link to Reds Meadow Pack Station:
http://www.redsmeadow.com/pack-trips.htm#Dunnage

Also check out Muir Trail Ranch.

Check out these two options:

http://www.coloradotrailhiking.com/

Colorado Mountain Expeditions. Supported segment hiking of the Colorado Trail. Under their FAQ, they state: "The only criteria for bringing children is that they are strong enough to hike long days with big elevation gains." Obviously your toddler on his own wouldn't be up for such a hike, but if you're prepared to put him in a backpack carrier when he tires out, it might work. You could certainly try contacting them to ask more questions!

http://www.glacierguides.com/za/GG

Glacier Guides. Guided rafting and hiking in Glacier National Park (including overnight backpacking, and optional Sherpa service). They offer custom trips, too, which might be the best approach for your family. I don't know if they have any age limits on their regular backpacks, but if you went with a custom trip I suspect they could put together something which would work well.