You should be able to find a concrete contractor who is also capable of doing masonry retaining walls. They would need to demolish the old walls and regrade the property to create a wider driveway. Then they would need to rebuild a wall which could be poured in place concrete or brick blocks or another retaining wall material. Once they have done that, then they would pour new concrete. in that portion of the driveway. You can discuss with them the options for the new concrete drive. If you find a talented concrete contractor, they should be able to handle the whole job for you....... Your other option is to hire a general contractor who would be capable of managing the entire project for you and bringing in the proper sub-contractors to do the work, but you will pay a bit more for this option......

Have a look at the permeable paving products. The stones look good too, can be a bit difficult to keep them in place though as they can spread around.

Try diggers paint brush restorer. Small patch first, you don't want it to spread it. Failing that there is a company called So Safe. It produces graffiti remover and will get rid of that in minutes. My guys use a lot of it with very good results.

Jacey, nice to see you are still here, many aren't after this length of time. I'm having a little chuckle here as when I originally read your post, my first thought was "move house", but I didn't want to sound so rude as to say so. It reminded me of my first house which was at the flat end of the street but the other end was very much "mountain goat territory" and the driveways reminded me of yours. After living in the homes for years, some spent mega amounts removing rock and excavating to create a garage more at road level and from there the stairs started zig-zagging to the front entry, new front entries were even created at a lower level, but the stairs still continued inside the house, there was just no escaping the climb. I wondered how you even got your wheelie bins up and down the drive. Hope you are enjoying your new home, long term I think you made a very wise decision.