I would go with that grand stand. I would not waste the money on a hydro wb unless you live in the mountains. I would set a budget of $800 or less for a walk behind and settle on a belt drive. You will find it handy, but you might use it a couple hrs a week unless your yards are tiny with lots of gates. I would rather see you get a 25 inch ybravo or exmark 30inch mower then spend 2k on a 36 wb. With a 36, you will still need a smaller push mower. The ybravo and exmark 30 fills both roles.Edit - I mentally had 5k in my mind to spend for a trailer and a mower.
Ran out of time to edit last post.