My dad uses a Simplicity to mow a 2-3 acre section of his property and he loves it. He picked it up from a laker having a garage sale. They had taken pretty good care of it and had all the service records to prove it. He also has an old Wheelhorse with no mower that he uses to pull trailers around the property and he had an old Gilson for about 15 years too. Both of those were my Grandpa's before he passed. Grandpa was a retired mechanic and he pretty much collected old mowers fixing them up and trading them off for the next project.

My uncle rents an acre or two from mom and dad and mows that with his John Deere. He seems really happy with it. Their neighbor swears by his John Deere as well. He has an acre or two that he mows for a yard and another four or five acres that he mows trails into. However, I've also heard a coworker that raises horses and has farmed that John Deere's are known to be awesome tractors with not so great mowers on them. He says the mower decks the mower decks have a reputation for being difficult to keep aligned, so they always cut at a slant. My uncle hasn't really had any issues with that as far as I know. My neighbor's yard has always been immaculate, so I doubt he would put up with a sub-par mower.

Personally, I think you'd be fine with either. I haven't personally met anyone who has regretted buying a John Deere or a Simplicity. With a space the size you're looking to mow, I don't think you'll have too many issues either way. Most the issues we've had come from running them too long at once. Doing more than an acre or two, you need to worry about things like burning up belts from the mower deck getting too hot. Mom and Dad have 7 or 8 acres total. They don't usually mow the back half, just the front 2 and the 1 or 2 that my uncle rents get mowed on a regular basis. If you try to do the whole property in a day though, you can pretty much count on toasting a belt or screwing something else up. For that much land, you really need a commercial mower. Sticking to 2 or 3 acres, we haven't really had any issues. Less than an acre, basic maintenance should keep pretty much anything running.

I don't know anyone with a Kubota (most people I know are as broke as I am), but I've never heard anything bad about them either. Trading in at full price sounds like a good deal if you plan to trade it in. We've always bought used ones and sold them after we upgraded to better used ones, so I couldn't tell you what to expect from trading in a John Deere or a Simplicity. I can tell you they both do well in backyard deals, so imagine they hold their value reasonably, but I doubt you're gonna get full price on them.