No reason a decent auto upholstery shop couldn't do something similar. But you'd not be able to with the SERG parts. The newer post-04 tour pak racks are different and these would not come close to working.
No particular one could not get one of the older style tour pak racks. They had a little cracking issue that has to be kept watch on. It's a nice little addition to look at though.
We have a few upholstery shops around - will do some checking - the jester would need a little different style but think it might work. Will print out your pics as a reference since my ability to explain this would never be as good as your pics.
As the proud new owner of the jester (in 07) with leather tour pack, I noticed the MoCo "forgot" to finish it with the piece that drops down, behind the passenger's back, that covers up the ug-buttly area under the tp & the rear fender. May get that piece done as well. Of course the Moco "forgot" a few other things about this bike, so am just glad I did not have to pay extra for luxuries like axle nuts.....
Your bike looks damn good, Don. Damn good!

Mike