I especially like that you have included the price of these items:
"Medical treatments - poison ivy and thorn stabs - $50
Physical toll - ughhhhhhh....."
I have also done a lot of work at my farm while close to being broke and therefore hard labor was the only option.
My rule has been to start the job with the tools that I have available, until I am experienced enough to determine my "best" rate to accomplish that task. I then go on to Pond Boss or youtube to find out the best way to do it with better tools or more horsepower.
It frequently turns out that more horsepower is a good value, if I value my time and physical toll at anything more than minimum wage. We have several good equipment rental places in town. They are too expensive for things you will use more than once (for example, buy your own good chainsaw), but they are great for horsepower.
I don't even own a tractor yet, but I can rent a 33hp kubota - and frequently do. I can also rent the attachments that I only rarely use. However, I also rent mini-excavators, backhoes, cement mixers, etc. and use them on the weekend so I can get a lot of work accomplished and only get charged for the 8 hours on the engine meter.
I can then step up to the commercial rental places for bigger equipment. I can rent a D8 dozer or a 365 excavator, as long as my credit card allows their deposit requirement. (My area does not have steep slopes or rocky terrain, so they will rent to people with zero training. I don't know if that holds true around the country?)
I have learned that there is almost always a "right" tool for the job. You just need to be able to determine when you have to pay extra for the exact right tool, and when you can get by with the less than perfect tool, but can still safely accomplish the job.
Good luck on your project!
