Hi and Welcome!
I see your also a Georgian Bay boater, we boat out of Queens Cove in Victoria Harbour, just 15 minutes from you. I own a 298 as do our friends we boat with, so congrats on your new purchase, we love our 298 as do our friends with theirs.
Our friends have the Hurley Davitt system for their dinghy, as do another couple we also boat with. Both seem to like the system just fine, and your right, the swim platform on the 298 is fairly high, but they don't seem to have serious issues getting the dinghy onto it. It does take both of them to lift it on, but I've never seen them throw their backs out or anything! Below is an image of it, and I'm sure they would recommend it.

cheers
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2004 Four Winns 298 Vista
"Last Minute"