Well, it depends on what you need/want to do on the land. If you are moving any dirt at all, or substantial amounts of brush. A mower just won't do. If you are looking for a do-all machine that is well suited to mowing, but can handle some other tasks, here are a few on the "smaller" end to consider:
Kioti CK20
BX series Kubotas
Simplicity Legacy
TYM T233, T273, 330HST
Of these the CK20 and TYM's are probably the most capable, all around. Of course JD, NH, MF, and others also have machines that would fit your needs. All of these are well made, good choices. Wow! This list covers quite a range! You have to clarify your uses and select the right machine for YOU. Remember: heavy is better for ground work, light and nimble for grass.
I went through similar thinking some years ago. I bought a large JD garden tractor (425 AWS). It's great for mowing and snow removal. But, many times I wished it could have done more. So, years later, I bought another, bigger machine (Kioti CK25). Now I have 2 tractors; both ideal for their intended use. But, had I bought bigger to start with. I would have saved some serious dough in the long run. A bigger tractor will generally do anything a smaller one can. But, not visa versa. Sometimes a smaller tractor will do it more easily (my little deere will snow plow circles around the CK25 on confined driveways and walks). But there are many things a bigger machine can do that a smaller one simply cannot - not strong enough, not tall enough, not heavy enough.
Of course a serious tractor commands serious bucks. So, don't expect to get it done for a grand or two. Unlike buying a car, consider that it's a long term investment, on the order of 20 years or more.
There are many posts on this topic. All of this has been addressed in these other posts. Read many, and then read some more. You'll then know what direction to take.
