Redbud can be readily limbed up to allow for walking underneath. Mine is fine. It is Minnesota strain since regular ones may be cold damaged here on the cold edge between z 4 and 5.

Witch hazel is more shrubby in form IME and will take quite a bit of pruning to get a tree-like form that you can walk under. I have one vernalis and virginiana, both natives, which do well here. It is too cold for the Asian witch hazels in my immediate area.

I agree that crab and serviceberry are nice. I also like my Stewartia.

I have amelanchier canadensis in tree form and the berries are truly wonderful, if you can get to them before the birds do. I also have crabapples Makamik (pink flowers, fruit best left for birds) and Dolgo (white blooms and my kids eat the fruit fresh...I find it too sour). They’re hardy to my zone 3a, so should be ok for you as well. I’ve planted narcissus and tulips around all of them, and I’m training clematis on them. Hope this helps! Have fun shopping! :)

I have two Centurion Crabs. They would tick all your boxes, except fall color. Not much to speak of. A Kousa Dogwood would be a better choice for 4 season interest because of its showier bark.

Kousa dogwood in zone 4 sounds pretty iffy to me :-)

Autumn Brilliance is pretty much the standard serviceberry you see in heavy use where I live (zone 4), but I have also grown some Snow Cloud that did fine. What exact hardiness zone are we talking about for "upper midwest"? As for crabapples, you might want to look at upright and columnar crabs only if you want to be able to walk under/around them. I've seen people trim spreading crabapples up over head height at a young age and make them into hideous umbrella/palm tree shapes. And if you wait until they are bigger, you may have giant branches to remove that may wreck the tree's natural shape for awhile. Some good, narrower uprights are Gladiator, Rejoice, and Red Barron.

A few other options you could look at are Amur cherry (Prunus maackii) and showy mountain ash (Sorbus decora.) Both of these tend to be fairly fast growers, in my experience anyway. Two trees I haven't tried but might also be worth a look are Pink Flair cherry (Prunus sargentii - zone 3 claimed) and tree form Nannyberry (Viburnum lentago.)

Beyond zone (I am technically zone 5a) I wouldn’t recommend a Kousa dogwood or native Cornus florida if it get below -20F since that seems to be their limit as far as making it through a winter undamaged. Somewhere like Cleveland which IME doesn’t get that cold would be fine.

I think Im on border between zone 4 and 5. Appreciat e the specific cultivars - Im off to google images! I was looking at pics Allegheny serviceberry - seems larger/more full than Autumn Brilliance?

I got to this site via a link on the University of Wisconsin Extension web site. The small tree search page I linked to appears to provide a lot of choices.

https://www.landscapeplants.org/plants.php?tid=Tree%3A+Small

I love Amelanchier, but they do tend to get hit pretty frequently by disease issues around here. Leaf spot and cedar rust are ubiquitous on the Amelanchiers I see planted in my z5 area (both species-type alnifolia/canadensis/laevis and the grandiflora hybrids like 'Autumn Brilliance'). My alnifolias also get besieged by Japanese Beetles in bad years..

On the upside, the aforementioned diseases usually only cause a cosmetic issue with the leaves, and not a threat to the plant's overall health if it's in otherwise "happy" conditions. The leaf spot and the rust don't usually affect the berries too much either!

Rose Family trees are also subject to fire blight in areas where that occurs.

One of the small buckeyes with pretty flowers that I can't grow, but you probably could.

Morton Arb lists Kousa as Zone 4 hardy. Some others have it at 5. So perhaps, Zone 4 would be risky. Another tree that has done well for me is Winter King Hawthorn. It would be at the top of your size requirements, but IME, the berries are showier than the crabs and their color persists longer into the winter. Also has that nice peeling orange and cream bark. It will also extend the flowering season, because it flowers later than most of the trees in the landscape. (Early June).