I've posted in a couple of threads about haying equipment because I just got into doing all aspects of haying this year. We've always had the land, done the cutting, raking and hauling of the square bales (between 5,000 and 12,000 per summer, depending on the year and if we were doing some to sell), but we never baled it ourselves (also never messed with rolls). Due to issues with the custom baler's increasing unreliability, I decided to pick up the equipment to do hay from start to finish. Due to the size of our operation, used equipment was the only option, and since I was going to be trying to roll most of it, the size of the roller was a large concern, because my tractor is only 45 hp.
I'll have to say that the stars aligned perfectly for me, because I found a New Idea 484 roller (makes a 4' x 5' roll) about 20 miles from the house and it works great (got a thread about that one) with my tractor. I picked up a Kuhn GMD500 disc mower just about 4 miles from home (and I have had to replace a bearing on it - there's a thread about that). Just a couple of weeks ago, I got a New Holland 256 rollabar rake, and it was about 20 miles from home, and it is great (just had to grease it and clean a bunch of old, crusty oil out of the gearbox). I also picked up a John Deere 24T baler - didn't have to do too much to it other than get the twine threaded correctly through the needles and it promptly punched out 300 bales. On all the the equipment I got, I've had to spend a few hours on each getting it ready to go, and I'm sure there will be problems with them in the future. However, I've also picked up all the manuals that I can find for each piece of equipment, PM'ed them as well as I can, and have gotten pretty familiar with them so I'm comfortable I can maintain them and fix them as required. Plus, with the balers, I at least have a back-up of sorts; if one fails catastrophically, hopefully I can use the other.
I think it is a great convenience to be able to do all the hay myself without having to worry about someone else's schedule, someone else's breakdowns, someone else's sickness, etc. However, I also think that haying is not necessarily as complicated or critical as some folks describe - no offense intended to anyone. Of course I love to cut hay, let it dry, and bale it; but everytime that it's been rained on, it dries out as well. Of course it hurts yield and quality, but it's not the end of the world if it gets wet, in my opinion, so long as it dries before you bale. Also, since now I have all my own equipment, I don't have to do all of my hay at one time - I do it in sections to mitigate the risk of poor weather or equipment failure. You could do the same thing.
I was lucky with some of my equipment finds and have about $6,000 invested in the equipment listed above, and found it all locally - and some of it really was just good luck and word-of-mouth conversation. I'd say if you want to give it a try, go for it, and invest in the proper equipment. Odds are that if you don't like doing it, you can probably sell the equipment at a minimum loss and be richer in experience.
Good luck and take care.