This is from someome I know with a degree in forestry and is an ISA Certified Arborist.
First of all, there is no perfect tree. A tree that is planted correctly in the right place will grow, thrive, and do well. Any young tree (including oaks) if planted properly will grow fast.
They are trees. They have leaves or needles, some have seeds or flowers, and they will drop them. Deal with it.
Trees do need maintenance. Trees are an investment. You take care of your investment and you reap the benefits.
Second, it is a myth that trees cause cracks in things like water lines. 99.9% of the time there is a crack (however minor it may be) or moisture seeping out and a tree will do anything to compromise that by going toward the water source. But, the tree is NOT the initial cause, it is the already cracked pipe, that is usually very old in most cities.
Third, the best trees to plant are those that are best for the site. It sounds like an open space, so the biggest thing to consider is the soil and type of drainage for the area. That will dictate the proper species to plant.
Are you trying to convert a field to a wooded area and are looking for hundreds of seedlings or saplings? Or are you planning more of an open space area with a few dozen individual large trees? The answer to that will dictate the type and size trees you plant (and can afford). If planting several larger trees you would do best with 1 1/2-2 inch size trees that will transplant best. Going larger is much more expensive and has a higher mortality risk if not properly cared for.
I would highly recommend the website: http://www.treesaregood.com
There is a wealth of info there about tree selection and care.http://www.treesaregood.com/treecare/tr ... ction.aspx
Also, check your local county extension office, NRCS, or state forestry office for information or assistance. A local consulting forester or consulting arborist may also help. (Consulting arborists can also be found from the ISA website http://www.treesaregood.com
With all that being said, some species I would recommend do include oaks. Like I said, if planted properly, they will grow fast and thrive. Some species I like are Swamp White, Burr Oak, and Shumard Oak. Live Oak, Willow Oak, and Chestnut Oak will also do well for zone 8.
Maples will also grow fast. Newer species include Autumn Blaze, October Glory, and Freeman. Many are very low on seeds these days.
Hybrid Elms are Dutch Elm Disease resistant. Homestead, Frontier, and Valley Forge are popular.
London Plane Trees are great large trees. They are similar to Sycamore, but anthracnose resistant.
Baldcypress is one of my all time favorite trees and it grows just about anywhere, but loves moist soils.
Gingkos are fabulous and very tolerant. Make sure to get male trees that won't drop fruit.
Hackberry is very tolerant. Sugar Hackerry is great.
Honeylocust has varieties without the seedpods and thorns. Try Sunburst.
Kentucky Coffeetree looks pretty pathetic when young, but grow into great, large, hardy trees and you can get them without the seed pods too.
You could also plant dogwoods and crepe myrtles for lower growing trees in the understory.
I would stay away from cottonwood (poplars), willows, and pears.