need help with older side delivery rake choices

We are buying 23 acres of pasture land (around the wife's new dream home) and I want to put up small squares to help pay the mortgage and get into the hay business as a hobby to start with.  I am having to buy all of the equipment to start off (except tractors which are borrowed) and with paying too much for her house I am trying to acquire equipment on a budget.  In looking at used side delivery rakes in this area (SE South Dakota) you can find a few different ones and am looking for the good and the bad.  Using the 256/258 New Holland as the standard (which still bring $1,750-3,000 in this area) what compares to what else we can find,

 

JD 896 and various other older (640,660,670,671)

NH 56 (a few here and there)

New Idea various models all older

And then a few odd balls (oliver, allis, and the like that would be hard to find parts for)

 

I guess my question comes down to the new idea and older models bring $1,000-$1,500 and the nicer JD and NH ones can bring $2,500-$2,750 and with dealers close for each is it worth it and are they really that much better.

 

Thanks,

 

need help with older side delivery rake choices