Just starting out, which equipment to buy?

I won't be baling much, 20-50 acres. Currently my dairy farmer neighbor does it but he can't always get to it. He doesn't care if I take over doing all of it or just do certain parts myself and he'll take care of the steps that I don't have the equipment for. 

 

I'm in Michigan, these will be grass/alfalfa fields for sheep and cows. My current tractor has 40hp at the PTO and does not have remotes. I'm keeping my eye on the used market for something a little bigger with remotes. 

 

So which equipment to get first considering how I can piece this together over time? Start with a tedder and rake, wait until I figure out which tractor I'm going to use before I get set on a baler and haybine? Any certain style of each type of equipment to look at? The fields here are pretty flat if that makes any difference. There's a Sitrex 2 basket tedder at a local auction that I'm still liking the price on. They also have a Kuhn 4120 rake but that seems to have drawn some attention and it might go high. Would I be better looking at the older style equipment since I'm not doing that many acres, and it costs a lot less. Like maybe just using a wheel rake?

Just starting out, which equipment to buy?