I've carefully read every reply. I am not currently a business traveler. However, I want a set that would allow such a change. I may be traveling to Germany or Japan in the next few years as well. My selection of checked/carry-on/shoulder bags are intended to compliment one another and allow for mix and match scenarios. That in mind, I took a look at the Travelpro Platinum and Eagle Creek ES lines...

Checked Bag:
Tarmac 25
24” Expandable Rollaboard Suiter

Carry-On Bag:
Tarmac 20 Wide Body
20” Expandable Rollaboard Luggage

Personal Item Bag:
Deluxe tote

I'm not really impressed by their "personal item" bags that have the awesome warranties. For me, the purpose of such a bag is for valuables, fragile items, things needed in route (books, electronics, etc), and over flow from the other carry-on when there is no checked bag. Historically, this has been my laptop case du jour.

The Pack-It options offered by Eagle Creek intrigue me. But I have been considering compression bags as well.