Running fiber question.

Hi all, I'm wanting to run fiber from one end of the house to the opposite end.

I'm planning to get 6-Fiber, LC OM4 Multimode Military-Grade Armored Fiber Optic Patch Cable from FS.com, and two of these 3-Port Fiber Optic Wall Plate Outlets with LC adapters.

I'd like to learn the proper way for getting it inside to outside, and then from outside to inside. Then supporting the wire along my wood siding. I'm worried about the bend radius.

My plan: Cut a rectangle hole for the low voltage old work bracket, drill a hole big enough for the fiber to go through the exterior wall on both sides, ???.

Thank you!