Need help with dry horse haying in the 21st century

My 70 year old dad just moved up here to Massachusetts from West Virginia. He's an old school guy - Massey 255 with a sickle bar, bar rake, and square baler. His only "modern" update was buying a tedder a few years ago. His system in WV was to wait for 4-5 days of clear warm weather, mow on day 1, use the tedder on day 2, and rake and bale on day 4 (or day 3 if it was warm enough and the hay got full sun). Myself, I haven't hayed since before college.

Trust me, at 70, he can work most 30 year olds in the ground. The good news is that he has me to help now, and my son in a few years. Also, having retired early, I have a few dollars to help bring his methods into the 21st century to hopefully allow him to hay with a smaller weather window, make better hay, make it a bit easier, and who knows perhaps even hay for his neighbors. Plus, it's great to work with him again.

I've done numerous web searches, gathered conflicting (and often outdated) information based on situations not exactly like ours, and came out feeling more uneducated than when I started. So I'm hoping y'all can give me guidance on equipment and methods, as well as helping me prioritize what to buy first.

I guess I'll start with the hay. His old farm was perfect for dry horse hay. Some grass, timothy, alphalpha, and clover. His new place looks to be fescue and some weird cabbage and lettuce looking things. Needless to say, at a minimum he wants to add timothy. His idea is to get bags of timothy seed next spring and just walk the 40 acres and throw it. As for the cabbage and lettuce looking things, he is looking at them as "milkweed" - not ideal, but "not worth getting your panties in a bunch."

Mower/conditioners is where I originally started. I figured buying one would cut a day or two off of his window. Then I've seen everything from them not really reducing drying time for dry hay, to the flail type making clover and alphalpha useless, to allowing for perfect dry hay in 2 days. So I have no idea what type to get, or even if it is better. I'm not worried about the 255 being able to handle one. I've been thinking about buying a used tractor with a cab and a/c for him next year anyway, and keeping the 255 as a helper. I've been considering the JD 6410 MFWD.

I had better luck with rakes, and will probably pick up some brand of rotary rake next year.

He got a good deal on a NH 311 baler when he moved. So he's been working on it all winter, so we'll see how it does.

For the tedder, I've seen all sorts of advice from doing it how he does it, to using it as soon as you mow, to using it twice a day.

Any knowledge and/or advice would be appreciated. I also apologize for the numerous typos. I'm down to one arm (broke my elbow a few weeks ago) and am using my wife's iPad to type, which apparently thinks I do not know what I want to type. For instance it keeps autocorrecting tedder to Teddy Roosevelt. I tried to scroll up to proofread, and ended up autocorrecting a sentence to something unreadable.

Thank you.

Need help with dry horse haying in the 21st century