Research everything before you commit and figure cost and expenses against gains.
(1) Is there demand for Fescue hay on the local market, many people will not buy Fescue, is the market cow hay or horse hay. What does the mid summer heat do to fescue yields in your are. Is it a good clean field or need spraying.
(2) What package sells on the local market, big round, medium round, small round or square.
(3) Will people in your area pay extra for fertilized hay? Everybody wants fertilized hay but very few are willing to pay extra regardless of the benefits. Will the landowner allow overseeding of clover in the fall to increase yields and cut fertilizer.
(4) In the deep south you can almost guarantee that lime is needed in addition to fertilizer, to realize a good yield of grass hay will require a complete fertilizer in the spring and top dressing before second cutting, something like 250 pounds per acre of triple 19 in the spring and 100 pounds of urea later. If the land has not been limed in the past several years the fertilizer will only be roughly half as effective. If there is broomsedge growing in the fall and winter it needs lime, a soil test is best before you make a deal.
(5) Don't buy junk equipment, dont buy a 50 year old sicklebar mower and expect to cut 30 acres of high yielding hay if you have never set up and worked on a sicklebar mower before. You can do it without breaking the bank if you take your time and do the research, brand new 5' cut drum mowers cost around $3500.00 and can be used with a 30 H.P . tractor, it would cut 30 acres in 8 hours or less depending on the hay and ground speed. Decide what type of baler you will use and then choose a rake to fit the baler, you don't want a side delivery rake if you are using a 5X6 round baler and you don't need a 10 wheel V-rake for a small square baler.
The bottom line is this guy wants his land mowed for free, if you take the job on you will have to get something out of it. Based on my own area I would guess you could pay for roughly $12,000.00 worth of equipment, the fertilizer and make a profit or at least get some favorable tax advantages over 5 years. You will have drought years but you will also use less fertilizer in those years and hay prices will go up so it usually more or less works itself out.