Our Quaker Meeting (church) sits on five acres of land, a couple acres of which are lawn, with similar terrain to your description, some of it sloped, some of it kind of bumpy and uneven. It takes more like four hours than eight to mow. Nonetheless, we have been through way too many riding mowers. We finally decided that cheaping out does not work in this case and we need to buy ourselves a really good mower, regardless of price. We are in the market for a new one now and expecting to spend $5K. Especially to be snow plow capable, the cheap ones are so flimsy made these days, it isn't worth it.
In your budget, if you have a trustworthy source of good used reconditioned mower, I would consider that above new. The people that repair mowers (whom we have gotten very familiar with!
) say that quality of construction has declined considerably in recent years.
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