My sage advice is simply, if it's less than 5 acres, grow a garden and buy a riding lawnmower. It's not worth the aggrivation. Used hay tools are just that, used and probably with issues. I certainly don't off my hay tools until they start having issues, then trade in/sell outright and buy new (always new, never second hand). I'm not teying to insult anyone, every operator has to start somewhere. I started with some ancient equpment (NH Hayliner 66, Ancient JD side delivery roper rake, Ancient NH side mount sickle bar mower) because I wanted to 'try' to see if it was for me with the intent of loosing the old stuff asap, which I did, but then I own a very modern machine,.welding and fabrication shop so fixing ancient junk wasn't an issue. All the junk went down the road, long ago (probably to someone who thought they could run hay on a budget.....)
Nothing more aggrivating and stressful than having a few acres ready to bale and the baler won't cooperate because somthing isn't working right and there is a thunderstorm due in, in 3 hours. Why play that. Garden and mow and buy your hay if you need some. Life is too short for that stress level.
There are more people (on here) running what I consider to be junk, with underpowered compact tractors that are marginally acceptable. Unless you are extremely fortunate and nothing breaks, you might actually get some dry, green bales in your barn, but the odds of that aren't good and rained on wet, molding hay isn't worth anything and it stinks and more importantly, it's a fire hazard.
I won't even consider any tractor with less than 50 pto to be acceptable for powering hay tools, preferrably 85 pto or better. Conservatively, I have around 250 grand in haying equipment (all I do is hay), my 5 acre at home ground gets mowed and gardened.....:thumbsup:
It's all a business expense, we are an LLC engaged in crop production (forage). Equipment gets bought, used and sold.
So yes, it's fun so long as everything included the weather cooperates but when something don't go right it becomes a nightmare real quick.
Do yourself a favor, plant a garden and mow the rest with a nice lawn mower. Your stress level will remain sane.