It depends on what you want to do. If you want a trail buddy and easy going all around for local shows, I'd pick Jack. I wonder why he never raced, he sure has a nice pedigree. I'm no expert but if you're not eventing or anything, I think his confirmation is probably fine.
If you want to do competition, then it looks like Roman has the temperment. I wonder if he needs surgery for the bone chip though. I would sure have him vetted before committing to him. Roman looks "hot" and I also read that into his write up. He probaby would not be as happy being a trail buddy and local all arounder.
If it were me, I'd take Jack, 100%.