Hello everyone and thank you for all your replies.

To answer earlier questions, this will be a weekly routine from Tampa to Connecticut (LGA / JFK), flying out Sunday night and coming back Friday night.

I went to a Samsonite store at a local 'outlet' mall and purchased the wheeled
Supra 7 duet garment bag
Product Size: 14.5" × 21" × 8"
Weight: 10.14 lbs
and Supra 7 hand accessory bag.
Product Size: 12.5" × 18" × 8.75"
Weight: 1.6 lbs

Was it a good purchase? We shall see.

In the future I may buy some accessories such as the:
Edimax nano router for hotels that only have a wired connection.

I've never lived or driven in snow, so Connecticut may freeze me to death unless I buy this for layering, Ice breaker 200 long sleeves
An overflow bag: Sea to summit bag

Any recommendations on a neck pillow? Preferably collapsible but not required.