I have a good example of why it is worth buying equipment - can't comment on running a farm, but with the construction industry, you're ALWAYS better off doing it yourself:
I spent this summer working the grounds on a property I recently bought. The grounds around the house and barn were cleared of trees, but had little else done, and that was 25 years ago. The soil is basically bank-run gravel, so not much grows. Existing grades needed to be redone for drainage, and cover was natural brush. The driveways (1100 ft. total + ~5000 sq. ft of parking areas) were made from natural existing material and were in bad shape - improperly crowned, rutted and rocky.
I graded the grounds and driveways using my tractor. I dug out hundreds/thousands of rocks with my FEL and backhoe. I brought in 360 yards of nitpack gravel for the driveways, and 235 yards of organic loam (poo) and spread and raked the products then seeded the loam, creating a little over 1/2 acre of grasses areas and about 1/2 acre of driveway surface. I also reluctantly did a jet-pump to submersible conversion on my well in the middle of the whole thing, which required digging a 100' trench for a new water line and power, re-plumbing the interior, etc.
I got a price from a driveway company to do the road work that I did - $15k + materials. The landscaping work would've been easily double that. I would guess that the well work would've been somewhere in the $3-4k range. Sure, it cost me 2 months of time, but I enjoy doing all of that stuff and I need the exercise. I spent about $10k on materials and supplies, put over 200 hours on my tractor's meter, lost 25 pounds, but knocked out a solid $50k in work, and likely increased the value of my property twice that. Also, if I hired the work out, everything would've ended up so screwed up, I would've had to do it all over anyway, since the vast majority of professional contractors are completely incompetent. I paid $15k for my TLB 5 years ago, so it paid for itself 3 times over this summer alone.
As far as a maintenance story; I recently bought a used 6' 3pt snowblower for the same property. I paid $1350 for it, but got a grading blade thrown in for free, so let's say it was $1000-1100. I'm going to spend $300-400 more to get the hydraulics working, so call it $1500 to make the math easy. I don't know what it would cost me to plow/blow 1100 of drive, but it HAS to be at least $100. We usually get about 8-10 storms a year worth clearing, so payoff on the blower system is 1.5-2 years.
JayC