Yes but you'll more than likely have to cut roots and there is always the risk you run with any transplanting only even more stressful than usual given there is less room for roots and dries out faster in a container.

Hey... crepe myrtle can serve as nature's "orange (crash) barrel" in this sort of location. We have a mid-stature cultivar at the corner of our drive where it warns/slows vehicles cutting the corner towards our fence post. While the trunks don't get big enough to actually stop a car or truck, hitting one will get the driver's attention and the tree will grow back as long as ANY roots are left in the ground. Ours was knocked over by a wide-swinging front loader and was back to full size within a few years. It has actually turned out to be a very nice tree for a location less than 2 ft off the drive . That said, seems knowing the hardiness and stature/cultivar of your plants would help with the decision. If yours are only reliably root hardy in your zone, you'll be cutting them to the ground every few years anyway. Stature matters because it needs a mature height of at least ~10 ft to get the branches above vehicles in tree form and crowns of the big (20+ ft) ones will cover a large portion of the drive dropping bunches of stuff into the small openings of anything parked beneath them.

I've read that propagation from root suckers is best done in the spring but in my stubborness I cut 3 suckers (white) yesterday, potted them and am keeping them moist in the greenhouse. Plesantly surprized this morning while working in the greenhouse to find 2 of the 3 sucker plantings finally showing new growth! Took 6 weeks. Still high and dry in MWC with our first frost of the season Wednesday morning. I didn't cover up the night before because the wind was so strong the covers would have probably blown to Texas by morning. I got lucky with only so slight frost burn on a couple of tomatoes and the squash. That afternoon a couple of the Superfantastic even had multiple blooms. Looks like I'll make it to next Wednesday (by the forecast)then harvest the green beans and squash for Thanksgiving. Probably a couple hundred of green tomatoes and several peppers. All and all with the fall planting and rejuvination of the tomatoes, I had a decent year despite all of the setbacks. Keith

I've got a similar area to deal with, although thank goodness it is still shaded with healthy live oaks. Tilling might help remove the more shallow rooted things, but for the woody growth and deep rooted stuff you will probably have to use something systemic that will kill the whole plant. And then you will have to wait until the plant dies, so it's not all that quick. Of course if there is nothing in the area that you care to save/protect, then something more radical that would really turn the soil up by going deep (like a disker or bulldozer, etc.) might eliminate most of the deeper stuff. I'm no expert (why not talk to one...a landscaper?), but that seems like the only way. I've got to be especially careful so as not to harm my oaks. I am going to use a poison that I normally use on mesquite trees which is a combination of diesel and Remedy (bought at feed stores). Diesel by itself often does the trick on woody growth. You can mix it and put it in a sprayer or pour some in a container and use a cheap paint brush to 'paint' it onto the woody growth. If you choose the spray method that is not meant to suggest that you just spray a broad area. Either way you do it, you must do each plant individually being careful not get it anywhere else BUT on the plant. And with this method you must paint/spray it all the way around the woody stem, not just on one side of it. Encircling the plant's main trunk this way insures that the penetration is even and completely goes to the plant's core and is eventually absorded by the roots. What I will do is cut each woody growth down to a stub and then paint the stub right away while the 'cut wound' is still open. And needless to say, one must wear appropriate protection (gloves, long sleeves/pants, mask) when working with this toxic stuff. The Crape Myrtles sound lovely but won't provide much shade, if that is one of your criteria. I planted a red oak about 10 years ago (it was just 4ft at the time), and now it's at least 20 feet tall and turns a lovely red in the fall. You might also look into other kinds of oaks or you might consider a gingko tree or two. Once established they are not susceptible to disease, are long lived and turn a beautiful golden yellow. I'm not sure where you live, but if water is not an issue then cypress might be pretty too. You might consider planting some that are evergreen and some that are deciduous. What I enjoy about the live oaks is that they stay green all winter until the early spring, and then quickly shed their leaves just as other decidous plants that have been leafless all winter are sprouting new growth. Some people plant deciduous trees purposely on the northwest side of their homes so that the sun will be able to warm the house in the cold of winter, while providing much needed shade in the warmer months. Good luck with your project, and hope you will share your process so we can all learn with you.