I have spent over 50 years of my adult life taking on neglected land, 5 farms in 4 different countries – England, Australia, Scotland and Portugal. It was all good experience. Four had a run-down house and buildings, one was bare land. I too had to build roads –my wife became quite adept at that job, more buildings, fences and clear large trees, scrub, rocks and stone, etc.
I did use contractors when it was more expedient to pay a professional for large scale works such as house building and underground drainage and irrigation systems rather than spend time and money doing the job myself, probably to a lower standard if I had done it, and involving the need to buy equipment that would not be used again. It is a good plan to always keep back some cash from a sale to be able to pay contractors when necessary on the new property. I brought land into production that had never even been grazed before. As I posted, I never needed an FEL. The one I had in the 1970s was only used once a year to remove the build up of FYM in a building over winter. I wondered why it is considered essential to have one in North America. People come to rely on things they have and do not consider other ways of doing a job.
At the same time I am a peasant. That is someone with little money that farms in order for himself and his dependents to survive and only buy depreciating assets if they are essential for that survival. Perhaps that is a different attitude of mind to those who can afford to go out and buy machinery and equipment. If I had had the money perhaps I might have bought more things too.
I also wonder what posters would make of the fact I have never found it necessary to buy a vice? A welder, drill, angle grinder/cutter were essential, as well as making my own cultivators, harrows, seed drill, etc., but bought sprayers because they are too complicated for me to make. Never needed a mouldboard plough after 1979 either.