Will this camera equipment backpack stand upright on it's own (assuming the top isn't loaded with heavy items)?

Not well, I usually lean against something. Helps to put something heavy and flat in the bottom.

How should I measure my laptop for this bag?

The details on the bag says; “ 【15.6 inch laptop compartment】 The padded upper compartment offers space, especially for laptops, MacBooks and tablets up to 15.6 inches.”

Will this bag carrier a d500 nikon and 300 zoom lens

i dont know the size of 300 zoom. you can take off all the inner parts and attached them as you want so i dont think you will have any problem. i use it for canon 77 and 11-16 lens, 18-55, 55-300, gopro, chargers, 360 camera. if your lens in not longer than the wide of this bag. than you dont have a problem. if its bigger than put the inner parts so the lens will stand from bottom to the top. its the best bag for camera and lenses, relatively small and very cumfortable. the best bag i ever had/checked/used.

Outer Material	Nylon
Material Type	Nylon
Shell Type	Soft Shell
Lining Description	Polyester
Product Care Instructions	Hand Wash Only
Item Weight	0.94 Kilograms
Item Dimensions D x W x H	9.39"D x 11.8"W x 17.29"H
Storage Volume	24 Liters
Unit Count	1.0 Count
Item Shape	Rectangular
Color	Gary
Pattern	Splicing
character	Grey
Backpack Design	Framed Backpack
Style Name	Classic
Number Of Pockets	6
Apparel Closure Type	Zipper, Hook and Loop
Water Resistance Level	Waterproof
Pocket Description	6
Compatible Device Size Maximum	15.6 Inches
Strap Type	Adjustable
Embellishment Feature	Cord

Camera Backpack, Beschoi Waterproof Camera Bag with Tripod Strap and Rain Cover Large Capacity Rucksack for Digital SLR Camera, Speedlite Flash, Camera Tripod, Laptops, Lens and Accessories

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