As Hayman1 said "don't get greedy, never cut more than you know you can handle at one time. Repeat after me... This rule also saves you from loosing the whole enchilada to rain that was not forecast."
Be realistic...35 acres ain't all that much hay that you would need super duper equipment. I have done as much as 100 acres of grass horse hay for my own race horses every year for the last 20 with some decent, old, but well cared for equipment. Start with a good big tractor that is very reliable, and a smaller one to tedd and rake and move wagons. It sounds like you have that. I stack directly on the wagon behind the baler. Then pull the wagons into the barn and unload when it is convenient for me. I leave the last loads of the year on the wagons and use or sell directly off the wagons. My wagons never leave the farm and some cost as little as $400.
So if you do 5 acres at a time like in paragraph #1, You will need 5 good wagons (100 bales each) and a place to drive them in under roof. After raking and baling all day, you will be glad to park the wagons for the night, and go have a beer. I am not a fan of throwers, because you still have to manhandle the bales at least once.
I use an old NH276 baler that is a workhorse. But I have a backup NH270 in a pinch. I have 2 of everything, one good one for use, but an older but serviceable piece if the good one has a flat tire or breaks down, just when I have 5 acres of choice hay on the ground. Try to be consistent in your purchases. If you start with New Holland balers, stay with them because every piece of equipment has its quirks and a unique parts supply chain, so you don't need to be in a constant learning curve for different stuff.
I am an old horse guy (I'm old, not the horses) , and I still do about 40 acres of hay a year. It is just me and a couple part time after work guys. Due to a bad back, I never touch a bale. I race horses, so most of my hay goes to the track sometime during the year, and my surplus is sold to other race horse guys.
My whole farm and equipment is designed to be cost efficient and relatively easy for a lazy old guy..