I would vote for some Oriental Raisin (Hovenia dulcis) trees, various types of American/Asian Persimmon trees and some Pawpaw (Asimina triloba) trees for starters...

Smaller Rusty Blackhaw Viburnum (Viburnum rufidulum) trees and large Witch Hazel (Hamamelis virginiana) shrubs would also be nice gap fillers.

Here is a link that might be useful: favorite underused trees

oaks are a good choice especially if you have gravelly soil.
possible species:
Red oak (like u mention)
White oak
Bur oak
Black oak
Post oak
BlackJack Oak
. Tulip poplar would work but it tends to break easily in high winds

A few other ideas:

Black Mulberry (Morus nigra) Tree:
http://homeguides.sfgate.com/growing-conditions-mulberry-tree-46263.html
Dioecious, so need male & female for fruit...

American Smoke (Cotinus obovatus) Tree:
http://homeguides.sfgate.com/american-smoke-tree-problems-67205.html
Despite its rarity, the American Smoketree is easy to grow. It is tough enough to tolerate rocky alkaline soils and long droughts. Young plants in sunny locations can grow rather rapidly, up to two feet a year.
http://www.treetrail.net/american_smoketree.html

Sourwood (Oxydendrum arboreum) Tree:
http://home.howstuffworks.com/sourwood-tree.htm

Magnolias:
http://www.usna.usda.gov/Newintro/magnoli1.html

Fringetree (Chionanthus virginicus):
http://www.directgardening.com/detail.asp?ProductID=5180

Here is a link that might be useful: Magnolias

Jrobinson, do you have any issues with overhead power lines in either yard that could make large trees a bad choice?

I love the tulip tree. Lirondren tulipfera or something or other in scientific terms. It probably should not be planted where it can grow over your house.

With the oaks, pick one with fall color. Also if them holding their leaves all winter is a negative to you then pay attention to that. I have a young scarlet oak, Quercus coccina I believe. It seems to be a leaf holder and I'm not sure how I feel about that.

I'll second Toronado's recommendation - For an oak, I'd pick Scarlet Oak (Quercus coccinea) over Red (Q. rubra) since the fall color is much better, more reliably red. Red oak CAN have good color, or they can just turn a bland brown. Scarlet oaks almost always have at least good color, and many excellent deep red.

White Oak (Q. alba) is another possibility. Slower growing, but not really *that* slow, and a good red-wine or purplish fall color most of the time.

Sugar Maple (Acer saccharum) is, IMHO a better maple than Autumn Blaze or even the red maples like October Glory. Although all would be OK for your situation.

FYI, A happy American Smoke Tree Cotinus obovatus can grow ALLOT more than 2'/year. Key to this species is the drainage, and not planting it where it gets an excessive flow of water (i.e. near a gutter downspout).

Our Q coccinea holds winter leaves as well, though not over the entire tree. Supposedly many Oaks hold fewer leaves as they mature. Time will tell for us.

I suggest you also look into American Yellowwood Cladrastis kentukea. When these are fairly mature trees in the peak of flower, there is not much more beautiful. Here at least they also have excellent yellow fall color. They seem to grow about 2'/year. Have seen them used as parking lot trees in landscape islands, understory trees, and open space trees.

Got to bring up Three Flowered Maple Acer triflorum as well. One of my personal favorites. Ours has been much faster growing than what is claimed by most sources. Bark is beautiful, and last year it defined the color "orange" is fall. In spring, it is one of the earliest to leaf with bright emerald green leaves that are rather ornamental themselves IMHO. Our tree will be leafy, while virtually everything has done nothing, or almost nothing.

Last suggestion is another fav. Acer luecoderme Chalk Maple. Basically a faster growing, tougher, more drought resistant, smaller Sugar Maple.

Arktrees

For the front yard, it sounds like you really want something that looks nice vs. having to provide shade.

Although there's a seperate conifers forum, a Dawn Redwood (Metasequoia glyptostroboides) might do the trick, or another, very similar deciduous conifer, Bald Cypress, Taxodium distichum. Both hardy in Ohio, and both are fairly fast growing (sometimes VERY fast for the Metasequoia) deciduous conifers with good orange/rust fall color (but this is variable).

Chinkapin oak, Yellow Buckeye, Katsura tree.

Yes for the front yard aesthetics is paramount to shade. I really like many of the suggestions, but for availability reasons I specifically liked the the sugar maple recommendation. Is the Sugar maple superior to the Autumn Blaze? Are these trees clean? I have terrible memories of having to pick up fallen limbs from our trashy Silver Maples growing up. I don't want that.

Also, I know I will be getting very small specimens, but what is the opinion of buying trees from a place like Direct gardening?
It is hard not to like their prices, seems like there is much to risk. What am I missing?
http://www.directgardening.com/

Lastly is it a bad idea to plant a tree in early May. Should I just be a little more patient and wait until September or October to plant them?

Thanks for all the ideas so far!

Re: Direct Gardening -- according the website that rates various mail order sources, you should avoid this one like the plague. 381 negative comments versus only 146 positive. This is pretty much a case of you get what you pay for. In this case, not much.

As to planting times, it depends on where you are and how you care for it after planting. Landscapers all over the country put in new gardens throughout the growing season without issue, provided watering is attended to properly.

"I live in SW Ohio" - in much of your region typical soils are clayey w/relatively high pH. This will limit your options. I would avoid trees that dislike higher pH, like scarlet oak. Locally sourced shumard oak would be a possible sub for scarlet oak, and it often has better fall color than red oak (although as hairmetal said red oaks can at times have good red fall color).

Sugar maple is probably OK if your soil has decent drainage. Autumn Blaze will tolerate most soils, but I'd recommend Redpointe over Autumn Blaze. "Are these trees clean?" Depends on what you mean by "clean" - most mature trees will have some litter issues. Sugar maples will have seeds. Redpointe doesn't seem to produce a lot of seeds. A few of the rubrum maple varieties are seedless, but rubrums (like October Glory) often become chlorotic in higher pH soils.

Tuliptree, yellowwood, yellow buckeye, & chinkapin oak all do well in your area (chinkapin oak generally doesn't have good fall color), but these all prefer decent drainage.

Early May is a great time to plant trees in your area. Just be careful to water adequately if the weather turns warm and dry.

I do live in an area where most of the soil near has a good amount of clay in it, but my town's soil has a good bit of sand and gravel. My yard drains like a spaghetti strainer!

But I have no clue on pH, what does it cost to test that?

What greenthumbsdude said, plus Nuttals oak, Willow oak and Shumard oak. These are red oak family oaks. But quercus Alba (white oak) is the best oak in the northern climate, but slower growing than the red oaks.

Soil with good drainage gives you more options. You should be able to find a soil pH tester at your local garden or hardware store for under $10, but based on your location it's unlikely you have acidic soil.

Smoke tree is short lived. You may have already planted it, though. Swamp white oak is great, if you have less than perfect drainage. Even Water oak is good if you have a soggy area. You have many options. This is an old post, though. I hope you planted what was great for your yard already.