Has anyone used this on American Airlines underseat item?

Yes, I recently used it on AA and it fit nicely. So glad I didn't have to fight for overhead bin. I zipped in my seat and out with this bag!

Does the front pocket have any useful organizing slots or pockets or is it plain inside?

Yes. There are useful organizing slots in the front pocket.

Will either of the side pockets hold a water bottle?

There is only one side pocket. You can fit a bottle of water (not a water bottle) in the side pocket, but it won't zip closed.

Fits under seat & possible to fit: dress shoes, 2 pants, 3 dress shirts, 3 socks, 5 men's underwear, laptop, 1 shorts, 2 t-shirts?

In my humble opinion, all your clothing will fit. I used the under seat spinner as a second luggage. (Just in case my main large suitcase was lost) I packed more for a 5 day cruise. Enclosed was 2 dresses, 2 leggings with blouses, 2 shorts, shoes, bathing suits, makeup bag, wigs, curling irons and toiletries. It was full and tight but it fit. In your case I would hang my slacks and shirts as soon as you can. I hope I’ve helped with your question. Enjoy

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Shell Type	Soft
Material Type	Polyester
Item Weight	2.5 Kilograms
Storage Volume	2.89 Liters
Item Dimensions L x W x H	13.5"L x 9"W x 16.5"H
Size	One Size
character	Sports
Pattern	Solid
Color	Purple
Strap Type	Stretchable
Is Autographed	No
Lock Type	Combination Lock
Capacity	176 Cubic Inches
Handle Type	Telescopic Extendable Handle
Additional Features	Wheel, Laptop Compartment
Wheel Type	Spinner
Number of wheels	4

Samsonite Underseat Spinner with USB Port, Purple

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