I likely would have started with a mid design and scaled up to condo sizing. The advantage of a mid is 360 deg rain protection, lower wind profile and lower weight. I suspect you will find that the sides collapse into the tent when configured like the bottom picture in any wind. The shelter is literally a sail (I am guessing at least 32 sft.) and I suspect you will have some redesign to do. (Your timeouts are going to have to be really strong. As far as end rain protection, i believe you will have to do a combination of longer tarp AND a solid waterproof end. That is a tall height to try protecting and you would need a REALLY long tarp, like a total of 15-20' to get rain protection from even a 45 deg rain coming from either end.
Here is a couple photos of a conceptually similar shelter, tarp and net inner, though I was looking for the smallest functional space not a palace. The inner can also be set up separately for open views in buggy non-rainy weather.
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With tarp and inner.
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inner only