Like Allen said, I'd be very careful about snooping around unasked on personal property. Most guys assume (correctly) that a snooper is a potential thief. Good way to get off on the wrong foot. I wouldn't mention you snooped and wouldn't say anything about the tractor that couldn't be discerned from the road. If you couldn't see it from the road, ask about the item that apparently grabbed your attention in the first place when first meeting him. After this, I wouldn't recommend snooping again. On how to talk to the guy... I am working on a 60 I got from a guy I sprayed crops for this past summer. He was standing right there as I unloaded my machine and I noticed an A under the trees. Just making casual conversation, I mentioned I was looking for a two banger to play around with and asked what his plans were for the A. By the end of the conversation, I learned he had another A and a 60 and all were for sale. Turned out labor was more important to him than the money or the tractors. We set a dollars per hour and a selling price. I gave him my number and it took him 6 months to get back to me on it. Like the others said, don't be pushy. I'm now working off the 60 and have it half "paid for" and I'm doing what I enjoy - farm work. The best part about it is that I'm working on the tractor in my free time and he has been a very good source of info on it. When he saw what condition it was in as compared to what he remembered, he dropped the price a bit for me without me asking. I eventually want a 730 diesel and an unstyled B to compliment my 60. Good luck on getting that diesel.
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