My grandfather milked 33 gurnseys on a 250 acre farm. My dad kept about 15 black angus around for beef and sale on a 100 acre hobby farm. Sure is different now. A couple of operations have moved in to West Michigan here from California. These guys milk 2500-3000 head. Milking operations are 24/7. Even the "family" farms that I grew up with, kids I went to school with, have grown to milk 200-250 head.
I spoke to one of my highschool classmates a few weeks ago, and he said they would always like the milk prices to be a little higher, but they weren't getting along too bad. Of course, this family has been around awhile and tends to operate debt free. Keeping those interest dollars in your own pocket can make all the difference in a marginal situation.
I don't miss the twice-a-day milkings, 365 days a year. But, it was a good upbringing. Everything else has seemed like a cake-walk by comparison.
I think if you can succeed in ag, you can do just about anything else.
Andy