Congrats, Andy! That'll be quite the change! Towing that distance is roughly equivalent to two round trips to Lake Powell for me. I left the boat down there a lot, but I still probably put 10k miles or more towing back and forth over the last few years for weekend trips.
Anyway, I was lucky...
Anything taken with an iPad or iPhone should have no problems uploading without any resizing necessary. I'm looking into a workaround on the server file size cap, which it turns out is actually 20 megapixels (I mentioned 16 elsewhere by mistake).
I had an elevated helm on our second Benny and I could swear that the seat wasn't actually any higher off the main floor than the non-elevated helm was. I'm probably wrong, but the point is that I would have loved to raise the seat on both of them.
I did quite a bit of work with the local canvas shop as well (enclosure and cover modifications). When I buy my next boat, I plan to order it without the factory cover so I can get it customized to my needs right from the start.
On what kind of device? (iPad, Mac, Windows, etc.) The previous poster had their browser in private mode and putting it in regular browsing mode fixed it. Check and make sure that's not the case for you.