I'd let Glider build it. At least I'd know he knows what he's talking about and doing... and I'd also know where to go if something went on the fritz. LOL... :s
Plus, he already has a good idea of the kind of bike I like... so that's a good start!
I believe I would go for a Boss Hoss bike with V8 engine and customed fiberglass body with a large seat for the wife. A neighbor of mine has one and spent a little over 53k but man oh man - what a bike. He even opted for a matching trailer.
for a custom bike, who would you choose to make it? I like the bikes that Indian Larry made and also some of the bikes that Russell Mitchel makes. Not much into the stretched out bikes but some of them look sleek in design.