I'm going to give some advice that may not be popular on here, but here it goes.
To make money farming, you do not need all the big equipment everyone is suggesting. In fact, that is a good way to not make money farming. One of the more successful farms around here is over 100ac and the only tractor they have is an old B-series Kubota (maybe 25hp or so). They do direct market beef, poultry and pork and let the animals do the work. The tractor is only used for the occasional mowing around the fences, tilling, moving things around the farm, turning the compost pile, etc. They buy what hay they need which greatly reduces the size of tractor needed. There is a good book by Joel Salatin called 'You Can Farm', it explains the whole concept in good detail. Joel is a little out there on some things, but making money farming isn't one of them (and all of his monetary principles coincide with Dave Ramsey).
My wife and I are getting started in a similar operation and the only two tractors I have are a '53 Ford NAA and a B3200 Kubota. I make 500-700 square bales of hay a year with that combo as well as doing all the work around our farms.
Now with all that said, if you simply want to be a 'gentleman farmer' and not really care if the farm is profitable, then by all means buy as much tractor as you can afford.
Personally, If I were in your shoes (can you tell I'm a Dave listener too, lol) I'd buy a good 4wd compact tractor with a loader in the 30-40hp range (L series Kubota, 3000-4000 series Deere). It would do all the mowing around a farm, building fence, gardening, cleaning out barns, moving materials, grading driveways, and light field work. Just keep cows on the land during the growing months and you avoid the need for hay/big equipment altogether. Also if you run enough cattle you won't have the need to do much mowing anyways.
Attached are some pics of me doing farm work with what most would consider a miniscule little tractor: