Amen to what Jogeephus said... It's been my experience that bought hay is usually lower quality than what you can make yourself, sometimes A LOT lower! Oh, I'm sure there's a pencil neck aggie type who'll whip out a calculator and "prove" you can't afford to make hay unless you have a bazillion acres. We've always baled our own hay and done a little custom work on the side to help pay the bills and I can tell you we've come out WAY ahead over the long haul. Plus, as Jogeephus pointed out, I KNOW I can make WAY better hay than most of the stuff these guys are selling, because I've seen some of the stuff they bale! I just fed year old hay today and when I unrolled that bale it was as fresh and green and smelled like sweet tobacco! From my experience the bigger the custom guy the more likely you are to get screwed. I've seen em cut 8 foot high seeding out haygrazer, leave it in the field for the better part of a month, rained 5 inches on it, the regrowth over a foot high and he raked it up and baled it. Probably found a sucker to pay big $$$ for it too! I stay small, do my own and a little extra and do my best to do it right.
Now, that said, no you can't make it pencil out with new equipment. The aggie type would be dead on right with the bazillion acre estimate if you're trying to pay for new paint. New stuff is really not worth what it's priced at IMHO. Everything now is electronic bell and whistle overloaded automatic everything whiz-bang gadgets and all you need is a bottomless bank account. I'd put my hay baled up with a 18 year old drum mower, an auction special home-rebuilt NH rake, and a 26 year old Ford round baler against some of these new equipment haymaker's stuff anytime. The only good thing about the new balers is that they do make a tighter bale (if you're storing outside uncovered over 1 year you can tell) and the netwrap is kinda cool but more $$$ and hassle at feeding time. The older baler still has it beat $$$ wise because you can build a pole shed or carport to store the hay in and it's easy to see that a soft bale stored under cover on a pallet will be better than a tight bale stored uncovered on the ground.
Haymaking is all about how it's handled, not how new the equipment is.
The basics are a good mower, a rollabar rake, and a decent used baler. No way can a little guy afford new. I'd prefer a well kept used belt baler to the little M&W type 'soft-core' or fixed chamber balers. For a mower I'd look for a good used Kuhn or NH. Just check it out carefully because there are a LOT of junk mowers out there. Turn the gearbed by hand several turns, grab the disks and try to make them wobble side to side, etc. If it locks up, grinds, wobbles, etc. pass it by. Rebuilding disk mowers gets very pricey very quick.
I lean towards the rolabar rakes (NH, etc.) because of their versatility. Sure everybody brags on wheel rakes and there's a ton of them out there, some pretty cheap, but a rolabar rake can do a lot of things a wheel rake can't. It can, if properly set, pick up more hay than a wheel rake. If your windrows get rained on, you can set it up high and unroll the windrows so they can dry. No wheel rake can do that. Wheel rakes don't like curvy irregular little tree, barn, or other obstacle infested fields like a rolabar can handle. Wheel rakes like wide open rectangular flat or gently rolling fields and really shine there, but for everything else, the rolabar does a better job. Wheel rakes also don't like tall grasses like johnsongrass or haygrazer very well and usually end up balling up or making lumpy windrows where a rolabar rake just keeps flipping it over and laying it out straight. In REALLY short hay like dry common bermuda or fine thin bahia a wheel rake WILL get more hay than a rolabar, but again the versatility is lower. With a rolabar, in thin hay, you can just keep rolling those windrows over onto the next swath til you get it the size you need, something you can't do with a vee-rake.
Yes you do need to get some mechanical experience, but I've never met a really good farmer that wasn't (or didn't shortly become) a fair mechanic anyway. Oh, there's plenty of the "lease it- don't grease it" crowd around but I see them go broke all the time. With older equipment you will have more problems, that's true, but you can make a LOT of repairs for what new paint costs and it should be remembered that even new equipment isn't immune from breakdowns. In fact older equipment that is well maintained, simpler in design, and usually (but not always) built heavier CAN have fewer problems than newer stuff that is over-engineered but under-built. Yes, as someone pointed out, you can lose a cut or watch it get rained on or burn up for a week waiting for parts and repairs to the baler, but that's just part of farming. Again, you can afford an occassional lost cut or poor quality cut for what you save over bought hay. You can have a barn full of shiny brand new equipment and if the weather is against you or you don't know what you're doing still put up poor quality crap or lose a cut to 3 straight weeks of rain. It happens to everyone. That's just part of the fun of farming.
Good luck and take it easy! OL JR