Thanks for all of the great feedback so far!
UPDATE - - -
We started "crate training" with the Sherpa bag on Wednesday. It's going MARVELOUS! He had two accidents Wednesday morning on the kitchen tile when we had briefly left the room to grab something (he was baby gated in the kitchen at the time, not in crate)... SINCE then... no accidents in the house AND no training pads used in the last 48 hours! He's eliminated outside everytime!
In addition to crating, we have gone to scheduled meal/water and water times and scheduled out times as well as taking out after naps, play or if he's out with us and starts to sniff.
Don't worry - he's had plenty of out crate time with us, but if we can't eagle eye him - he goes in the Sherpa bag. He really seems calm and I think he likes it in there. It's a very good size for him.
Today was also his first day at the office and he was perfect. I kept his Sherpa bag on a chair next to me.
After looking at crates at Wal-Mart and Petsmart and being pretty disappointed in what they had, I ordered this Suncast one from Amazon today and hopefully it will be a good replacement for the bag at home. If he transitions well to it, I'll get a second one for the office and probably just use the bag in the car and on planes.
Amazon
I can't say how thrilled I am that crate training / converting from pads to outdoors is going so well. We haven't gone on the grass yet... but he is dominating the concrete patio... lol
Sidenote - During the day we're doing breaks for potty/outdoor exploration or playtime or water and snuggles every 2 hours, max. At night he has been doing fine left alone from 10pm - 1am and after our 1am potty break, up for potty, breakfast and playtime between 4:45 and 5:15. He's still young... 14 weeks so he does sleep quite a bit. We try not to let him sleep from 6pm - 9pm otherwise he will be up every hour in the night.