I ordered the Eagle Creek Tarmac 20 in the palm green color this evening from Zappos. Zappos always sucks me in because if I don't like it, I can return it and it is free shipping both ways. You can't beat that. I also have 365 days to return it, not that I want the box to be sitting in my house for 365 days, but I won't be rushed to return it before my trip in case I change my mind and decide on a different bag or find a better sale. Zappos also had a pretty good price (cheaper than most other sites and the cheapest when you factor in the free shipping).
My deciding factors were:
1. The detachable piggyback clip which I guess would be what I would use to hook the bag to my other wheeled bag. I have had this clip on other bags and never knew what it was for. I have always used it to attach my fleece jacket or my pillow (I never travel anywhere without my pillow).
There seems to be some sort of disagreement in regards to if the Hovercraft 20 bag has this piggyback clip. I read this comment on ebags regarding the Hovercraft 20:
The bag did not come with the water bottle holder or add-a-bag clip that Eagle Creek advertises. We talked to both Eagle Creek and Ebags about this. Eagle Creek was not responsive. Ebags corrected their description based on reality not Eagle Creek advertising.
2. The cool little built in shoe box and stash cache which I only discovered today when clicking on one of the links on the Eagle Creek site for this bag. I am a sucker for gadgets and little hiding spaces. It could save me from taking a couple of little bags to put stuff in. I'm not sure if I would waste all that space with shoes though since I can cram them in along the sides but I'm sure I could find lots of other stuff to put in the shoe space.
Although the Hovercraft 20 is still another possibility, I think I will wait until my Tarmac 20 arrives. Ebags seems to also have free shipping to Hawaii and a 60 day return policy. If I decide I still want to check out the Hovercraft and time it just right, I could order the Hovercraft closer to my trip departure date and have both bags to try out when I start packing. I could then make my final decision with time left to return the bag I don't choose when I return from my trip.
I appreciate all the comments and suggestions. I think just writing it all out and organizing my choices helped me visually to see the pros/cons. It is good to hear from other solo travelers on how you handle traveling with luggage. It can never be as bad as my first trip to Italy. Boy did I pack badly on that trip. I learn a little more each time I go and I am looking forward to this year's experience. Especially not having to lug as much on my back and shoulders.