My goal is to have a nice sampling of fruit for my 3 year old to have as he grows up (currently he's not that into apples, but who knows if that will change). That said, I'd like to keep somewhat similar looks with deciduous trees, and nothing too large.

Here's what I'm debating between:

1) Anna's Apple & a Peacotum
or
2) Flavor Grenade pluot & a Santa Rosa Plum (these two seem like they'd be different enough, i hope)
or
3) Burgundy Plum and Anna's Apple

The peacotum is 500 chill hours, so (given this winter) we could end up with no fruit. That said, it sounded like the most interesting, though I love the idea that the Flavor Grenade fruit can hang on the tree for a long time (ha, if we had no birds) and of course I've heard the Santa Rosa is the most reliable.

What do you all think in terms of taste or experience? Anything else you'd recommend?

You might also consider a Flavor Finale pluot, it's even later.

It won't look the same but the right fig, like Kadota, would harvest June and August till frost. There should be a place for a fig in most landscapes. A three year old that likes fruit would probably like figs. They can be an acquired taste and now would be the time to learn. Very healthy food.

For a winter fruit Hachiya persimmon or in fall Fuyu persimmon.

And as for figs, yes, i love them and grew up with them and we've got one growing as a volunteer under a palm tree (very tiny, but it seems happy there next to an abutilon), and one that we just transplanted from a spot where everything dies (I'm blaming the eucalyptus), so hopefully that will do well in its new spot. We must have figs, I agree. And I actually am eying a persimmon too.... Thank you!