You will need to find a pro to do the new design I guess . I am confused as to why this drive takes the trip to the front of the house at all. The garage is on the side and IMO that is where the driveway goes and a nice walkway from there to the front door not driveway at all.From what I see a nice wide driveway to the garage on an angle and no driveway to the front of the house As for you doing the work that will depend on your skill set.Also do you have the equipment to do the work? Building a proper driveway takes skill and some major equipment

My husband is an expert level DIYer. He built a patio one summer with a guy who worked for a company that sold EP Henry pavers who knew how to do it and where to source the materials. It was a lot of work and the area covered was about one tenth of the area you're looking at (or less). At least half of the skill of DIY is knowing what you should and shouldn't do. Just breaking up the existing surface of your driveway and having it hauled away is a big job. Investigate the local codes to determine whether you can move the access point of your driveway so you can have a more direct approach as Patricia suggests. However, if you live on a road that is difficult to park on you probably want some parking area and maybe a turnaround. A paving contractor might be all you need. Get a couple to come and make suggestions and bid on the job. Then you could DIY the landscaping. That's something you don't need to do all at one time so you can spread the work out over weekends if you have day jobs.

The driveway leading to the front of the house is where the previous owner or the one before them closed in the single garage or carport and added a room and everything to the right.

The original front door is to the left of the chimney.

Here are some layout suggestions:

There is only 1 driveway.

How does thta help at all I see no point in the 2 driveways at all .

If you want to deal witha slope, you need an --person cconsultation. You pics don't show a slope. I would put a straight driveway from the road to the garage and remove most of the existing driveway. You have a llot Of concrete in your yard. You'd need to add more to get a bettebetter turning radius. Drivewaysvand concrete are not attractive.

A reputable designer ..addressing your needs….using road base…no concrete or pavement …would be appropriate in your setting…and the least expensive..we did that in our similar situation 20 years ago and it is still working today…

This shows the slope better

Road base is a mix of tar and pea gravel …which will need to be spread and packed down…with a roller…so it doesn’t move when you drive over it…a nice country look.. as opposed to black top ..

A good ground cover that flourishes ..with no upkeep ..St.Johns Wart..stays green year round…seen to the left of the steps….we live on a hillside…behind the house…that would be a nightmare to maintain..that is also covered over the years …beautiful and no maintenance as well

My apologies and thanks to Dig Dug for his rendering. I was going to suggest a circular driveway but he beat me to the punch. I modified his concept to include a round circle instead of oblong as easier to maneuver.

This is going to involve a lot of heavy equipment and dump truck loads of waste removal, and new materisls. If you were a backhoe operator with contacts in the industry, I would say DIY would be in the realm of possibility for you. The materials cost and equipment rental will still be substantial though. Several tens of thousands. Plus permits with the city, county, or state. Whomever controls the road cut ins and address maintenance.

UPDATE: We decided to at least do the "demo" of the bushes. I failed to mention that we have a tractor with attachments. After unsuccessfuly trying to "salvage" two bushes, we decided to take our chain saw and cut all of the bushes down on the inner side of the driveway. Then, we took the grapple and started knocking over and pulling the roots. After that was the bucket to start picking up debris and moving it to the forest (6 acre lot) in low areas. Here's what it looks like:

Good job. That will look great.