How to bake squash in a way that I can get cubes for my baby?

I baked lots cubed butternut squash for my twin toddlers this past winter since we grew a bonanza of squash last summer. I think hacking the squash into rough quarters first and then peeling it is easier. Having a flat surface on a chunk of otherwise slippery squash makes it safer to handle. Also, Rosle makes a veggie peeler that makes peeling squash and pumpkin a cinch. I baked the cubed squash with a light coating of olive oil, a little salt, 4oo degrees, time depends on the size of the cubes; start with 15 minutes, then check every 5 until it is how you want it. But at this point, give up on squash -- it is out of season. Move on to fresh asparagus steamed until fairly soft, baby turnips boiled and coated with a little butter, or even some mild radishes. My kids have enjoyed all of those spring treasures lately. And don't forget golden beets -- much easier to clean up than red beets!

If your baby is eating sweet potato, I'd just stick with them and not worry about the squash. There's not a big difference in the nutrition, and you've got the hang of the sweet potatoes already. (Stop when you're ahead!)
Speaking of buying squash that's already cubed, supermarkets have it too.
Also, I wondered it it's just a bit slippery for finger food. You could wait until he's using a fork.

Sympathies on the only having 5mimutes to get anything done in- I know what you mean! When I chop butternut squash, I don't cut lengthwise first. Once I've peeled, I cut it into round sand cube the circles. Cutting a round off the squash means that for the most part there's no dealing with the seed bit, and once you get your knife in a bit, it's pretty easy to cut through. You could peel and chop in 5 mins this way. If you're not a fan of microwaving, then I'd probably toss in oil and shove in the oven for about 20 mins, but it depends how big your chunks are. Cutting squash into easy to hold strips would probably deuce the time needed.

After baking it, purée in a blender and freeze in ice cube trays. When frozen solid, place cubes in freezer bag. When you are ready to use you will be able to thaw just the amount you want.

Packaged is what I meant! Usually in a disposable tray with cling wrap over it.

And in addition to Trader Joe's, Whole Foods usually has cubes of butternut squash packages in the produce section.

Ugh, that's PRE-cubed, not "per-cubed"...

If there's a Trader Joe's near you they sometimes have per-cubed butternut squash. A bit more expensive, but might be worth it.

Thanks. My heart aches at the last squash I ended up wasting because he would not eat it.

So I was wondering if there is a way I can figure out exactly at what point to take the squash out of the oven where it will be done but firm enough to cube,

Chopping before hand is not going to happen....I am not good with sharp knives and squash (I can barely cut one in half without injuring myself) and I literally don't have more than five minutes to do anything...so I usually chuck everything in the oven. I do this with sweet potatoes - they are similar in texture and they are dice-able.

I would also suggest using butternut squash. It's easier to peel when raw.

I peel with a veg peeler rather than a nice, which makes it a bit easier, chop into cubes, and microwave rather than bake, as they seem to keep their shape better.... It's also quicker! You could prep a big batch, keep them in a bag in the fridge, and cook a few at a time.

I'd suggest dicing before you bake--it's really not bad if you have a sharp knife. It will be hard to get nice cubes once it's baked, but you can definitely do it. Why don't you give it a try and if you decide you want nicer cubes next time, dice beforehand then.