Hog, I've been thinking about this for a few days now. I've been able to sit my fat ass on the bike and get some miles in. I think the seat can have a little more shaved off, and Jan at Woodstock Leather is willing to do what she can, but I think it will work out if modifying your seat is an option for you. Once the seat warmed up and it all compressed down, it's not as uncomfortable as before, so there is potential.
One of the other threads mentioned Alligator Bob in Illinois and I did speak with him. He's a nice guy, does great work, but would not reuse the stock cover and wanted to recover everything in leather after modifying the seat.
The other option I looked into is covering the cost of the tallboy seat, smooth backrest, and possibly the speaker pods, by selling the cvo setup. My parts guy printed up a quote for the cvo seat, rider backrest and mounting hardware, and passenger backrest; $2062.33 retail... the seat alone is $1879.12. I'd be happy selling all that for what I spend on the other stuff which I think is about $600.
food for thought