Well, don't pick a bike based on how comfy the seat is, because that can be changed out. As for your sit bones... you just have to break your butt in on the bike. If I don't ride at least 3 days a week, my sit bones are typically always sore when I get back on. Yes, padded shorts help this some, but will not completely fix the problem.
You have a lot of choices there. Maybe you should sit down, make a chart and list the components and your general feedback on each one.
You also need to know what you want and don't want. Do you want a full carbon bike? Do you want all 105 components? All Ultegra? A mix of both? Does it matter to you? Do you want a comfort road bike, like the Ruby or the Giant.... or do you want a racing road bike? Do you care about the color?
As for the double versus triple. If you ride serious hills, get a triple. You can switch it out to a double once you get stronger on the bike. But starting, you might want to get a triple.
By really narrowing down what you want and don't want... you can narrow down your search some.
Also, you said your budget is $2,000. Does that also include... bike shorts... clipless pedals... shoes... a tool bag with goodies inside... bike pump... water bottles... bike computer... new saddle... etc? That stuff and easily run up a $150-$500+ bill. EASY!
When I went to look for a new road bike (started with a Trek 1000), I knew what I was looking for. Once I found the bikes that fit my criteria, I test rode them. One bike stood out amoungst the crowd. When I rode it, it wow'ed me... and I knew it was the one.
"Life is not a journey to the grave with the intention of arriving safely in a pretty and well preserved body, but rather, to skid in broadside thoroughly used-up, totally worn out, and loudly proclaiming: WOW WHAT A RIDE!!!!"