Is there a way this might could be customized? Instead of being just plain black.

Hello. Thank you for your interest. Our Ideaspace money organizers are available in 5 pockets with limited designs. Here is the link for your reference. https://www.amazon.com/s?me=ADLNTWI4PEX2Q&marketplaceID=ATVPDKIKX0DER

Could I repurpose this to hold multiple checkbooks? Haven't been able to find a checkbook holder that will accommodate 3 or 4 checkbooks.

Reviews have said they have been able to put more money in each compartment than what was said. These will accommodate check registers. I do not forsee a problem.

Can I use this to travel by plane?

It’s much like a wallet. I purchased it for my blind mother to keep track of her $1, $5, $10, $20 bills. It’s a little larger than a wallet, so verify the size will work for what you need.

Manufacturer	Tidy Pockets
Part number	QR-183
Item Weight	141 g
Product Dimensions	10.8 x 1.27 x 20.96 cm; 141 g
Item model number	QR-183
Size	One_Size
Color	Black
Style	Black
Material	Polyester
Pattern	Solid
Shape	Rectangular
Item Package Quantity	1
Special Features	Zip Pocket
Included components	Card Holder
Batteries Required?	No

Tidy Pockets Money Organizer For Cash - Money Bag - Money Holder - Cash Organizer - Saving Money Organizer - With 4 Zippered Slots - Helps You Reach Your Savings Goals, Black, One_Size, Black

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