#2 because of the Liriodendron primarily.

I'd pick set 1. Don't have any personal knowledge of those. But what I've read online, they appeal to me most; I like the photos of their flowers and fall foliage on these best. I've read that Donald Wyman may not flower every year, for what it's worth!

Oops, Donald Wyman does flower every year, but I found this is what I read:

Malus 'Donald Wyman'
"This is a larger crabapple and tends to be wider than it is tall. Flower buds are reddish pink and open to large white flowers. Flower set tends to be heavier one year than the next, but this tree is always showy. Fruits are bright red and persist on the tree into winter."

I came across an Acer Triflorum at the nursery that carries Cladrastis Kentukea and Aesculus 'Homestead' (Octanda & Glabra hyrbrid)...hmm, leaning towards that one.

Also considering this combo:
Carpinus Carolina
Aesculus x Carnea 'Briotti'
Liriodendron Tulipifera

If 'Liriodendron Tulipifera' is a Tulip Poplar, our neighbors have one and in the fall it loses its leaves earlier than all the other trees.

"If Liriodendron tulipifera is a tulip poplar..."

Tulip Poplar is a very commonly used name for Liriodendron tulipifera, but don't say that out loud in this forum. It seems that calling it that can be politically incorrect in this forum and lead to long debates about "proper" common names. Hopefully, that won't happen this time....

Thanks for alerting me to an amusing thread, Brandon. Found it by searching "Tulip Poplar" on this forum. Hilarious how people can argue about the most ridiculous things!
BTW, it's my neighbors who refered to it as a tulip poplar.

I'd go for set 2, as containing the minimum of cultivars, and therefore the best for genetic diversity.

"It seems that calling it that can be politically incorrect"

Nope, not politically incorrect, but botanically incorrect - it isn't Populus tulipifera

Resin

Would you still go with set 2 if you could trade 'Golden Glory' with Acer Triflorum?

"Nope, not politically incorrect, but botanically incorrect - it isn't Populus tulipifera"

QED, it seems that calling it that can be politically incorrect in this forum and lead to long debates about "proper" common names.

The best time to choose (seedlings) such as Acer triflorum is when they are in fall color. It's the only time you should purchase this particular tree. It's perfect for you. These are the types of trees that need more presence in the community and among people. If they have Acer triflorum, they probably have Acer griseum... another to pick when in fall color. Both of these maple species are wonderful. Acer griseum is becoming more common now, thankfully. Acer triflorum needs more push though, yet.

Dax

I've always wanted a Acer Griseum but never brought myself to it because of the availability, growth rate and fall color variability (for the midwest, good for the east).

If for some reason I run into one in the fall, I will make a spot for it. I saw one this past fall, about a 6' but had poor/sparse branching.

I never heard of Acer Triflorum until I visited Chicago Botanic Gardens. The bark and habit is what leured me in. I would have never guessed Acer without seeing the tag. Shocked to see that a local nursery has large caliper specimans available...nervous to find out what the price is on Monday because I'm already committed, lol.

Here is a link that might be useful: Acer Triflorum Post

Set 1 for sure. I love 'Sugar Tyme' and the Aesculus. We have an old oak that is leaning badly toward the house and has been since we moved here 13/14 years ago. If it needs to go, I may replace it with an Aesculus since many oaks in our yard and throughout our area are having a tough time lately.

Fun question.