JEFF -Dad & I baled 20 acres of alfalfa hay,2nd or 3rd cutting with my Super H on the IH #37 baler one afternoon. No live PTO on the Super H and it was NO problem... even in some hills pulling a loaded hay rack... you just have to re-learn how to rake hay, small windrows, not the BIG monsters I raked when the neighbor had a #55 IH baler with the C113 CID IH engine on it, meaning I could clutch & stop anytime and the baler kept running.
ANYHOW...buy a RED baler... with yellow wheels, New Holland, I've NEVER heard anyone complain about a New Holland baler. The newer the better, but will be more money. IH balers tend to have fussy knotters, they waste a TON of time.
Any rake should be fine, a New Holland,IH, New Idea, Dad had a David Bradley (Montgomery Wards), about a 1950's vintage that worked fine... my Brother-in-law still uses it, His Dad bought it at My Dad's auction. Unless you get a wheel rake, the basket or parallel bar rakes all take a 7 ft swath.
An H FARMALL would be marginal running a PTO baler, but my Dad baled tens of thousands of bales with a '47 H & IH Cub engine driven #50T baler from 1947 to 1951, did custom baling down in Henry Cty. A Super H sells at a premium, especially a Stg II w/live hyd. An M would be a good baler tractor, also a Super M, and the faster gear speeds of the Super M & newer tractors would be better for mowing & raking. A Super M-TA also sells at a premium, but a 400 or 450 would be good, also have live PTO, probably power steering, would burn more gas, I'd stay away from the diesel versions that start on gas, run on diesel. A 460 or 560,even the diesels would be good too, or a 504, 544, or a 656.
The last built IH sickle bar hay mowers were good, they built a trailing mower, model # 1300,most parts are still available under a different brand name, think maybe Howes, or something. I've mowed with everything from a '39 H, '54 Super M-TA w/live PTO,live hyd, & Power Steering, & my '54 Super H w/live hyd & no live PTO. The Super H is/was the best mowing tractor, the SM-TA the worst when the sickle bar plugged up, and the '39 H took the most work to clear the plug, took something like a dozen pushes on the clutch. The SM-TA & SH both mowed @ 6-1/2 MPH, 7 ft swath, right at 5-1/2 acres per hour with no stops. The H @5 MPH, & 4-1/4 acres/hr.
The hay rake & mower should be fairly cheap to buy, they're old technology, everyone uses haybines & disk mowers now, the baler,not so cheap for a good one. You really need a place to store the baler & mower out of the weather. They don't take kindly to sitting outside.