@Nick S.
Hi Nick!
I'm not super familiar with this area in Illinois but I'll include a zone map to help you find some quick fixes- just figure out he zone specifically and go with a zone appropriate choice(s).
I'm thinking that you're maybe dealing with similar to Indy weather, so I'll tell you one bush here that works well year round and what most of our utility companies (at least back in the 90's and 00's) had running around electrical boxes in front yards.
Taxus cuspidata, the Japanese yew or spreading yew, is a member of the genus Taxus, native to Japan, Korea, northeast China and the extreme southeast of Russia. It is an evergreen tree or large shrub growing to 10–18 m tall, with a trunk up to 60 cm diameter.
It's just got to be trimmed back after a year or so to keep it from spreading too far out- these are the ones that you can shape into squares, cones, etc.
It's going to come pretty full and bushy looking, so you don't need to wait too long. It's going to look the same year round as well- so 'winter stable' in evergreen nature.
Go with odd numbers typically- usually (and I'm suggesting based on your picture) three on each side of the door.
I would not plant any trees- anything decent enough in size will cost a pretty penny. If you do plant tress do not go with a Bradford Pear tree- these are super popular in the Midwest at least and what far too many builders put in and still do as they are very fast growing. The issue is they are super soft, and one storm will break it down the middle or at the trunk if it's still small- avoid this one!
I can't see fully from the pics, but yes- you said power washing the roof as well- looks like maybe some fungus from the trees having been there and that will take some years off of the roof in looks.
I would go maybe with two smaller bushes at each side of the front stoop near the front. I would stick in some English Lavender right now as it should be in bloom until Sept/Oct. and will have a bright purple color- avoid boxwood bushes as they smell like cat urine.
I would probably run a solar powered lamppost where the stump has been ground -adding visual separation between the drive and walkway.
For extra eye grabbing attention and a homey feel I might add a small cement bird bath outside one of the front windows behind the Japanese yew bush. It will show nice as well maybe to have some birds visible from the dining or living room windows.
I would probably try to lay some grass seed as well and it should grow quickly without the trees giving off as much shade anymore. Don't have anyone out (I doubt this is in the works) for weed spraying, and be careful of overspray for weeds if you've planned on hitting the walkway and drive with weed killer, not letting it get onto your grass seed.
I think you can swing this one with 6 bushes, two lavender plants, a solar powered lamp post and maybe a bird bath and some grass seed for a quick an inexpensive fresh look.
Hope that helps!