Have 40 plus or minus acres of mostly wet grass [north of Seattle], with 3 acres in lawn, 5 acres in finish-mowed pasture and the rest in pasture grass either grazed or cut for silage on contract. I mow the 8 acres with:
John Deere 935 - front mower w/72" Commercial deck with a 60" flail deck for rough stuff and backup - 25HP Yanmar diesel - bought used 2 years ago
Massey Ferguson 1235 compact tractor with Woods 7200 rear discharge finish mower for groomed pastures. I leave the bucket loader on it. Bought new in the middle of last year.
Toro Wheel Horse 32" riding mulching mower - came with place, is beat to crap but still runs great and mows OK for tight spots when it's dry enough.
Sears 21" mower - my first mower, bought with my first house, it's 21 years old and never been to the shop, just new plugs & oil.
Stihl FS-200 brush cutter
Stihl FS-85 trimmer, with pruner and 11" hedge cutter
Stihl 026 chainsaw [plus 25 year old Mac chainsaw I used for college money cutting firewood--just used it to cut some 6" PVC drain pipe out of the ground yesterday - yes I dug it up with a plow by accident]
70's International 60HP loader tractor came with place along with several attachments.
Do my own maintenance and smaller repairs. Have excellent MF/Woods dealer 3 miles away and excellent but expensive JD dealer 12 miles away. Anything else is 40 - 50 miles away except for one ripoff Toro dealer.
I got my wife a Mule for Xmas as her garden cart [90' x 35'tilled area] but I use it for hauling my stuff and spraying [15 gal. tank from Costco]
My biggest challenge is getting good help, so I do most of this by myself or with the help of a really good neighbor. I'm still trying to come up with a better way to mow wet [I want to try double blades next year] and for trimming several thousand feet of horse fence. Any suggestions appreciated.