Check out Andrew Camarata on youtube. My favorite youtube channel.
He's a guy who worked for USPS and wanted to build a metal building on an undeveloped lot so he bought a backhoe, then an excavator, then a dumptruck, then a crane, etc. He buys all his equipment used and maintains it all himself. He quit USPS a long time ago and does work for hire with his equipment now that he has it all.
Andrew is where I learned that a regular joe could just buy heavy equipment and do the small excavation jobs contractors wouldn't touch. Sometimes he omits safety measures to the point that it's hard to watch (check out the recent bar sickle mower episode). So it's worthwhile reading the comments to find out what not to do also.
Before buying look at renting. There are pros and cons to renting, but most people won't use that enough to make buying cheaper, and renting means it is maintained for you.
1. My lifestyle is such that I only get an hour or two here and there to progress my projects. It takes probably 2h to go fetch a machine and unload it, so zero work would get done.
2. Around here rental machine availability is very inconsistent: it's quite likely that whatever machine you want is not available when you need it.
3. I've found that it's beneficial to have various attachments and accessories that most rental places don't carry such as a ditching bucket, pallet forks, brush mower.
4. I need to do snow removal in winter and although not necessary, heavy equipment comes in handy for that.
5. Other random things that arise when you own property: lift a fallen tree off your vehicle; unload palletized deliveries from semi truck, etc.
6. Typically the value of machines doesn't drop much, so if you have the cash available, buying machines with the expectation of selling them some time in the future means overall low TCO.
That said, I'd rent when I need a machine I would only use for one job.
He's a guy who worked for USPS and wanted to build a metal building on an undeveloped lot so he bought a backhoe, then an excavator, then a dumptruck, then a crane, etc. He buys all his equipment used and maintains it all himself. He quit USPS a long time ago and does work for hire with his equipment now that he has it all.