GREAT pics! The old ranches I worked up in WY had a few weathered remains of those old hay stackers and few old sleds slowly rotting away. Round bales put those things out of business.
I was noticing on the picture of your dad and the hand in the derby hat on horseback. Your dad appears to use his stirrups like I was taught, whilst the other gent uses his like I saw all the boyos up in Wyoming used theirs. I was taught to use the front part of my feet in the stirrups rather than sticking your foot all the way to the heel. Personal preference I guess, but it was a heck of lot easier to kick out and get loose if you got in a storm if your foot wasn't halfway in the stirrup.
If it had paid anything, I'd have stayed on the ranch, but I didn't look forward to being broke the rest of my life. LOL The cowhands up in Wyoming were making $400 a month, had a clapped out trailer to live in, and got three beef calves a year to eat. I couldn't see that, but I sure enjoyed the work when I stayed over during hay season and kept the equipment running for the hammer heads to tear up. LOL
A couple of the ranches up there still "roped and dragged" when it was time to work the calvies. We'd go help. THAT WAS FUN! You could rope til you missed three, then it was get off, and get dirty til it was your turn again.
They had a few hands up there that just never missed. Guess they didn't like gettin dirty. :)
Here's a pic of my uncle A. L. Lansford. Pictures were taken in South Texas in 1941. Allie (Al-E) was tougher than wet leather. I've got that Mod95 SRC that he's holding in one of the pics. It's down at Dad's in his gun safe. It's chambered for 30 US Gov't 1903. It'll shoot '06 stuff no problem. It's a hard kicking SOB, I'll tell ya that.
Allie shot it out with more than one bunch of Mexican bandits as his ranch was close to the Mexican border between Carrizo Springs and Freer, TX. Rough damn country. EVERYTHING sticks, bites, stings, or scratches in that country.
Allie wore a brush jacket like he has on and khaki pants 365 days a year. Never saw him with his pants outside his boots either. He died when I was a kid. He was a neat old buzzard.