The general consensus of opinion seems to be you can make money, break even while working hard, go broke or, multiple of the above in any order.
I trade labor with a guy who has all the equipment for round bailing. HE and his son bale my hay and I work for them an equal number of hours, sometimes using my tractor, dump trailer, chain saws or ... It works fair and we stay friends.
I have considered getting my own equipment but came out from under the anesthetic sufficiently in advance of the MISTAKE to avoid calamity. I have also had my place baled on the shares. That worked too but I prefer the barter arrangement.
I see a lot of new people getting into baling all the time but usually reality sets in and they get out within 2-3 seasons, worse for the wear. Same story on dirt equipment like back hoes dozers, etc. No one does a business plan much less a realistic one, lines up customers, realistically accounts for $, time, fuel, and other materials and repairs.
For some reason there is a never ending supply of people willing to risk a lot of time, money, and or expensive equipment thinking somehow they will be different and magic will happen and goodness and mercy will follow them throughout their days. These people make it hard on the folks who are trying to make an honest living doing things at the rates needed to pay all expenses and stay in business. The new guys typically think they can undercut the REAL people in order to BUY jobs and that sows the seeds of disaster. The REAL people may have it figured out pretty well and it is tough to undercut them and survive. The constant supply of people doomed to failure through failing to plan makes life hard for the REAL people.
Figure out costs, your customer base, and other ingredients of a sound business plan, ignoring unfounded optimism and a belief that somehow the weather will be your friend, you won't have unscheduled breakdowns, never get sick, always can find reliable help, and if you can't make a profit on paper using realistic inputs then DON'T leap into the tornado. If with realistic inputs you can show a good profit, then you might make it.
I have yet to have anyone bale my place and not have some kind of breakdown, sometimes minor and sometimes not. I have never had anyone bale my place that didn't have at least one other person on site all the time and at times I have helped out too.
If you can write an honest and complete business plan which puts you well ahead of costs then go for it and best of luck to you. If not then ask yourself why you think reality will turn out much more optimistically than your best plan shows. Wishful thinking is dangerous.
Pat