I go to auctions, so I have much less into my equipment than it would cost new, and that way I can afford to experiment on different ideas. When I bought my 5 acres I only had a 42" riding mower with a 12hp engine, blew the rod on that and scabbed another engine in it for a bit, then that one went out for some reason... went to Craigslist and got two heavier duty riding mowers for $300, one running with a 44" two blade deck, loved that thing then it broke a tooth off the input shaft in the trans... got the other one going that was a 46" deck 19hp with 3 blades, center one only like 13" long with the same size pulley as the bigger outer blades, didn't rough cut for nothing, and it was a variable speed belt drive (some are probably familiar with the MTD setup of the 90's, this one had low range though so it wasn't as bad) which isn't good for constant changes and gets cranky, the variable pulley is like $120 or so as well... Now I got a '97 Craftsman big tire lawn tractor with a 3 speed high low trans, 46" deck, 18hp pressure lubed Kohler for $350, the blades are all the same so rough cutting will be better once I go to high lift blades from the mulching blades that are on it. Also got a couple Snapper 28" riders, into the pair about $150, super maneuverable and do good at rough cutting so they can do the perimeter and around trees better.
Also got a tractor with bucket off craigslist, 26hp with loader and came with a 5' brush hog for $3500, works great for rough cutting tall stupid grass (reed canary), and got a 60" rear finish mower at auction that I have about $200 in now with new belt, blades and spindle bearings. The finish mower does great on anything about a foot or less, sometimes have to slow down or it will plug up but in the spring after things settle down can go in 3rd high or around 5mph
Things can be done on a budget, it does usually take some know how to get it working... nearly everything above needed some work eventually except the new to me Craftsman mower so far...
A couple years ago I was EXTREMELY CLOSE to getting a Cub Cadet zero turn mower with fabricated deck... was fed up with riding mower troubles