You are certainly right about the price of new tractors. My neighbors paid around $14,000 for a very silly looking, puny, subcompact, 21 hp Deer, with the "Estate Package" of stuff that they will never use.
I own a 35 hp John Deer, and a 24 hp Kubota.
Each of them had less than 850 hours on them when I bought them 6 years ago. I paid $16K for the Deer, and $5,800 for the Kubota.
Point is, never buy a brand new tractor. Tractors are built to easily last 50,000 hours, and can be very easily repaired after that. (In that respect, they are like the Post War Lionel Hog Locomotives.)
Find them in your neighboring farm communities on Craigslist. Cash and carry. Dealers are an absolute rip-off.
As for train oil, I just happen to have a bottle of 20wt Singer synthetic sewing machine oil on the shelf. Is that about the proper weight?
As for grease, sounds like the Red and Tacky may be the way to go.
I purchased a package of 4 products. On each bottle it says either: Gear lubricant, bearing oil or motor oil. These all have needle applicators. I also use a synthetic pin oil for rolling stock axles. I'll post a picture tomorrow. All of these are designed for model train applications.
I have a file on this subject = cut & pastes from various sources - primarily OGR Forum - send me your email address & I will forward my file to you & and when your read all = you'll be more confused than ever.
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