I'll add another thought, do you want a tractor? Is it something you would enjoy having around? Can you afford one? If so get one. If on the other hand it would seem like a necessary evil, I agree, hire it done.
I consider it a necessary evil in the same way that I consider the household appliances necessary evils :laughing:. I've never once found myself thinking "you know what I REALLY want? A clothes washer!" I'd love it if I never had to wash clothes or dishes ever again, or vacuum the house, or make meals, or ever do any of the property maintenance at all. I could spend all my free time playing with the trucks or other toys in my life.
But reality is that I'm just an average guy that grew up poor and somehow fell into a blue collar career in tech maintenance that now makes a bit over the national median salary. I do OK money wise, especially considering I'm now single and without kids, but I'd never be able to afford having someone come in and do all of the things that I don't want to do either.
I'm also thinking that this isn't going to be a once and done kind of deal. Especially with tasks like keeping the wash clean, and dragging the driveway and road...I've got about a 1/3rd of a mile of ground to cover between my property and the nearest pavement, as there are several vacant lots as well between me and pavement (house was built right before the market crashed, and the other planned houses here never went up, and I bought it near the bottom of it all), and I know dragging that road is going to tear up the lawn tractor.
To me, it's kind of like how I never wanted to _own_ a home either..I like the idea of not being in debt for the next 30 years by renting, and letting someone _else_ deal with all the major maintenance & repair duties, but I also liked basically locking my "rent" costs down to the mortgage payment which will never go up if I never cash out re-fi, and hopefully at some point in the future, the biggest chunk of that will disappear. From the time I bought it to now, my PITI has been less than what renting would have cost me as well.
But ultimately I accept that I will have to make sacrifices in some areas in order to get what I want in other areas. Such as how my daily driver is a 25 year old Chevy truck, so that I could afford to stay out of debt (other than the mortgage), and be able to have the two 4x4 toys in the garage too. Chances are that I'll never know what it's like to buy a brand new car or truck.
Can I afford the tractor? Well, that's kind of part of why I posted this to begin with...can I afford to go buy a $20K brand new one? No, absolutely not. I don't have that kind of cash sitting in the bank that I don't have marked for something else at this point in time, and I'm not willing to go into debt to buy one unless it becomes an absolute need. Heck, I wouldn't even want to drop that kind of money on a truck that I'd drive every day, much less something that gets far less use. But something used around $4K-$5K? That's doable. But then it's also a matter of I wouldn't want to spend that much just because I can if it's not the right tool for the job anyways.