Buy a used Highlift?

[Goodlife]

As many of you know I recently purcahsed 50 acres. It is a plateau on a hill and I have several things I need to do. Build a road up the hill, dig 2 ponds, level a spot to build a barn and another for a shed, and later dig a basement (in a year or so) for a house when I move there. And you all know I wil come up with a lot of other chores. I was getting ready to hirre a guy to do the highlift work to build the road which he priced at 5 days at $1,000 per day. That is $100 per hour for a 10 hour day which is not too bad around here. I got to adding up the other jobs I am looking for and came up with around $20,000 (my rough estimate) of work listed above. I got to looking on craigslist and I saw a CAT 953 for $20,000 (post says it runs good and has good undercarriage). I actually saw a couple in the $17k-$25k range. It seems to me it makes sense to purchase a used 953 to do my work and then after I am doen in a couple of years I could sell it and hopefully get most of my money back or just keep it. And I also figure if I had one around I would find lots of other uses for it such as clearing a few trees to increase pasture size. Here is a key, I can make it move and raise and lower the bucket but that is a long ways from being able to be productive. My brother has been a union operator for over 30 years however and knows not only how to operate the equipment, but how best to lay out roads etc... He would also be able to test drive equipment and know if it is working correctly and been kep up properly or not.

Seems to me the biggest risk is a breakdown thats expensive to repair. Of course this also means I need to come up with $20k+ upfront, but the advantages seem to outweigh these issues.

What do you all think? Does this make sense from an economic standpoint?