Help choosing the right mower

Fishyfish

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I have 2 acres with a few dozen trees. It is mostly flat with a shallow culvert in the front. It is shallow and wide enough that it shouldn't be an issue for any mower. There 1 steep but very small hill in the back that I have a push mower for. I will be towing a trailer to pick up branches and tow dirt. I have not moved in to the house and will not be fir 3 weeks. It will be 2 months overgrown when I get there. I'm looking to spend about 3K. I'd like to get a mower less than 10 years old, preferably less than 5 years old. Now for the questions. I think I've narrowed it down to a used JD X300 series, 350, 370, 380 or 390. Do any af them have serviceable transmission filters? Should I be concerned about any of these transmissions? Would the K46 of the x350 be an issue? Would the lower hp of the 350 or 370 really matter for my needs? I can get a model X500, 530 or 530 in my price range but am not sure if it will be worth it for my needs. I'm also open to other brands but don't know much about any of them. Thanks for taking the time to read this, any help would be appreciated.
 
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