I need to do some bit ticket items to my house - do I use a contractor?

Long story short, I bought a double a few years back in not so good of condition but in a great neighborhood. It has been a great owner-occupied rental since then, but I'm finally in a position to do some big ticket items: leveling the house, painting the exterior, adding central air/heat to the unit I'm living in, demolishing this 15X15 exterior shed, laying a driveway, redoing the fence surrounding the house....As these items are primarily exterior of the house, and not necessarily interior renovations, would my most efficient route forward be working with a contractor or getting individual quotes for each and going from there myself?

Any other comments are appreciated as well.