I'm firmly in the "Hire out the work on large machines" camp.
Firstly, I don't have the skills to operate dozers, backhoes or excavators, graders or such.
That being said, I designed my 8.1 acre property to have a 500-ish foot driveway, a house pad, clear a fence line, septic system install (code in our county), a new pond, 2000 linear feet of swales and needed clay mined for the clay plasters on our straw bale house.
When I moved to the new farm, I didn't know anyone or who to call to do this kind of work. But ya know, people know people who know people who can get it done. You just need to start talking to people and asking.
Our "little" projects were too little for the really big companies to bother with. But we found a father and son team who do all kinds of excavating work for folks around. They have the large equipment needed, the skills and the expertise to use them like fine carving tools.
Yes, it hurts to watch a dozer cut into the topsoil and start moving it around. And demolishing established trees on a fence line, but wow, so much work done in so little time.
Our excavator looked at me like I'd grown a second head when I tried explaining swales to him. But when I laid out the little flags and said I wanted 2 foot ditches along the hillside, he did what I asked. It took 2 days with the son operating the excavator and me running the laser level to get the 2000 feet of swales done. If I was renting the machine, or trying to do all the work myself, it would have taken a week or two.
Yes it can be expensive to hire out the work. Yes, you could buy the machines to do it yourself. Yes you could rent them. But there are some things that need done that you could do yourself, but can get done much cheaper and faster when you have a skilled worker do it for you.
After all, it is a community thing as well. And remember, if you have large equipment like that just sitting around idle, it isn't helping anyone and the amazing amount of embodied energy in them is wasting away. This kind of equipment should be used, and used often, or it is just wasted.
Alternatively, you could purchase a machine, do your work, and sell it. But that is another challenge.
Good luck with your projects, and remember, those dozer treads really tear up sod. But it grows back.