If I were you, I'd try to find a New Holland or John Deere side delivery rake. We have a very old JD that was given to us that I completely rebuilt for about $100.00. It is on rubber, not steel.
A wheel rake is okay, but a side delivery rake is much easier to control your windrow width with. Besides, unless you were to buy a new one, they are all ground driven. I have even pulled the JD behind my wife's quad.
As far as a sickle bar mower, you need to find an old sickle bar that is double action. The really old ones are single action and you have to go real slow.
IH made a pretty good double action sickle bar, the pull behind variety.
One thing about cutting hay with a sickle bar is that dry down may be a problem in the early part of the year as well as in the fall. You might need a roller crimper too. International made a really nice PTO driven, pull behind crimper. It's a model 34.
With a little creative looking, you should be able to find the crimper, rake and sickle bar mower for a couple of hundred bucks. Be warned though, you will probably have to rebuild each implement as they all have probably been worked hard. The good news is that the parts are still available for them.
A little note of caution, NEVER get your fingers between the knives and guards on the sickle mower. Due to the action of a sickle, the knives may roll over at the slightest movement and they will take your fingers RIGHT OFF!!