From the looks of it, water could run right around your grate to the door. If the walkway is sloped toward the grate on both sides, that would probably help when the rain is light, but when it is heavy it will run right around it.
I would install a grate that runs across the whole width of the walkway. Under the grate, I would have a trench about a foot deep with about 6" of gravel. In the middle of the trench, I would dig a hole another 24" or so deep and put your bucket with the sump pump in there.
It would also help to either move the trench closer to the door or grade the walkway so that the couple feet from the drain to the door slopes toward the drain. If you move it, it should at least be inside the "drip line" from the eves/overhang on the house.
Another option, if possible (hard to tell from the picture) would be to cover the walkway.
I remember Neillsville from "The Rock" radio station. ;)
So, to answer the question, we need to know where the water is coming from. You mention that it's due to a high water table.
As such, I'd not ever finish the basement. It will always be one power outage or one clogged drain away from being ruined again.
It also means that your dehumidifier will never 'win'. Basements are moist by default simply due to cooler temps, but if you have constant hydrostatic pressure, it will always be an uphill battle.
Your (what I call) interior footer drain will certainly help, but you're at the mercy of the drains always remaining unclogged and the sump pump always having power. You'll also have to make sure it can handle excessive rain during those big midwestern downpours.
If it was merely an occasional rain/snow melt issue, I'd feel OK finishing the basement, but given the high water table, I'd consider rethinking doing a full finish project down there.
If your water problems are primarily at the footer, It may be OK. As that is exactly what the drain system is designed to handle. But if you have actual cracks in the walls and water is coming in there, I'd be definitely be hesitant.
One other note...a bit further west into MN, the clay soil we were on had a lot of radon. So you may want to get a radon test before thinking of finishing the space as well.
Oh, one last comment: note that the systems being proposed are in no way 'waterproofing' systems. They are water abatement systems--in that they are designed specifically to not be waterproof and actually allow the water to come in so it can be moved out. It's a nit-pick, for sure, but actual waterproofing is an entirely different discussion.
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Some of the reasons might be: