WELCOME to these Forums...
You might also want to check things at
http://www.tractorbynet.com/
as to your questions...
Get a Kubota 4 wheel drive, (I have a grand L4200 with cab & loader).
A LandPride 3point Rear discharge finish mower if you want a finish mow... (I have the 7foot model)...
I would have a 3point snow blower, But I have a large blower attachment for my cabbed zero turn mower...
I recommend Kubota & Landpride because I Own Maintain and Operate them, I have had other makes over the years, but you will spend less money & time maintaining Good equipment.
Your $ budget will not get you what you want... but it will get you 'close' if you watch for Good used equipment... Spend More and get something With a cab, you will Not regret it in the heat of summer or the blowing cold of winter...
You are going to be Much better off with good quality used equipment than New low quality stuff.
Everything will eventually need servicing & repair, with the best quality equipment it will be Worth repairing... :smile:KennyV