The essential problem with a Bug Out Bag (BOB)

...is that we don't know where we're going.
Where is it that you are bugging out to? The Woods? which woods? For how long? A 2nd home?
Other?

Doesn't matter, if it comes time to bug out there must have been a good reason. Look at the last couple years with fires in the western US, if fire is coming toward your home then grabbing your bag and leaving is a better option.

+1, Eugene. You need a generalized, all purpose which will serve in a variety of circumstances.

Case in point, When i bugged out from a major wildfire three Years ago, I had no idea initially where I would end up. So I grabbed my bag, my cash stash, the pets, mrs. Hikermor, and hit the road.

The first, what was left of it, we parked in a quiet street. Second night, we got a room in a nice motel, courtesy of my BIL (He had point), and se spent three pleasant night there, retuning eventually to an intact home.

mY Bag had basics, FAK, water, a small alcohol stove, some snack, etc. I laded up on a three liter jug of water, and for good measure, threw in my CERT pack. Bugging out by vehicle is pretty simple, sheelter in provided by you wheels, and you probably have some basic stuff, already stowed.
Depending on you local situation, you should have a idea of what scenarios are most probable

Probably for most of us, a basic day pack 9the ten essentials)(plus a sleeping bag and stuff for a tarpshelter would do fine. Adjust for the seasons

This is my argument for packing light and moving fast. If you're light and fast you can simply go wherever seems best under the circumstances.

People's bags that weigh 50+ lbs bags with stuff dangling off of them decked out for rebuilding civilization in a Canadian pine forest in the winter make little sense to me unless they already live in a Canadian pine forest.

I pack my bag more like I am going for a long weekend where I might end up sleeping in my friend's yard and go target shooting one morning.

Pack such that you could rough it outdoors for a night or two if need be, but so that you could also catch a ride in the back of a pickup to a hotel or an airport and be drinking cocktails on a beach while your house burns down in a forest fire. The key is light and fast. And I also recommend having things sectioned off. E.g., firearms and accessories in an interior pouch so they can be readily removed.

Have your primary gear in a bag so you can be gone in less than 5 minutes.

Have your most important gear on your person. For me, that's cell phone, wallet, keys. Often lip balm. When traveling or abandoning abode, add passport. When permitted, include a knife and/or multitool, lighter, and a firearm.

If you have the luxury of a vehicle keep it stocked with some extra gear (with the luxury of a vehicle you could be ready to rebuild civilization in a forest pretty easily...) or have bins ready to throw into it quickly. But don't count on the vehicle being available during whatever may come, and be ready to walk away from the vehicle at a moment's notice.

Just my thoughts on the matter, ya'll do what works for you

I've had to un-stock our vehicles, unfortunately the one time you forget to lock your doors is the time some bored kids roam the neighborhood looking for unlocked doors. I think they have got me 3 times in 10 years, first time took a small bag I kept under the seat with a few supplies but they didn't find the stuff under the back seat. So I've kept them empty since and I've found the glove box and center console open twice after that.

I've had to "bug out" twice; neither was due to an issue at my location, rather they were family issues. First time was when the hospital sent my grandmother home for her last days/hours, so we had to grab and go. Second time was when my father had a meat grinder accident before they were to come to our place for Thanksgiving. We grabbed all our stuff and ran down there. Both times I didn't need any kind of wilderness survival gear, rather it was our normal meds, toiletries and clothing.
I've had two neighbors have to evac their house because it was on fire. First time was when I was still a kid living with my parents and those neighbors were a mile away and their teen aged son had to run barefoot through the snow covered road to our house to call the fire department. Second time was neighbors who dropped a blanket behind their drier and caught the basement on fire but we didn't even know until the fire department arrived as they had cell phones but were outside in the rain and all the neighbors helped out with raincoats and such.
A co-worker had to 'bug out' of his newly house when his neighborhood lost power for an extended period of time one winter. He took his family to a hotel for a few days until his neighborhood had power again. They had just bought and moved into their first house so they didn't have a lot of preps yet such as a generator so leaving for a warm hotel was the best plan there.

These are the more likely scenarios we need to prep for so I keep a set of toiletries and one of those week pill containers ready near my BOB as well as a change of clothes, shoes, coat, etc. Think fireman style with their gear waiting ready, before you go to bed lay out the clothes your going to put on in the morning and put your wallet, keys, etc in the pockets. Then if your house catches fire in the night you slip on those clothes and grab your stuff and go. No jumping out the window barefoot into snow and having car keys hanging by the front door which you can't get to due to the fire. That same BoB is my camelbak that I take hiking/biking/fishing, etc so its always stocked with some basics such as food and water. It sits on a chair beside my bed where I lay out tomorrow's clothes.

Hence modular bugout boxes. Just need to spend a night or two at a hotel or friend's place? Box #1 with spare clothing, toiletries, deck of cards.
Class 5 hurricane heading straight for Houston? Time for boxes #1 & #2 (always ready) plus #3-#5, who's contents were assembled following checklists when the hurricane's cone of uncertainty touched Houston.

One might not know what will hit but it is possible to assign the likelihood of happening to different scenarios and plan accordingly.
-Blast

Plus the modular box/bag method helps keep you organized even when you are not 'bugging out'. Where is my x gear, checks inventory spreadsheet, its in box #3

Good points - Have options depending reason for bug out and season.

Also, there is not nearly enough "wilderness" for all of us to bug out to...

I might back a sleeping bag for warmth, or to sleep on Aunt nancy's pull out couch.

My new-ish BOB includes work shirts, keycard for the office, & a laptop charger.

These are great ideas. I’m a big fan of keeping an emergency shirt in the car.

I'm curious now. What does the emergency shirt of the Great Chaos look like? A tactical polo? A travel shirt with many pockets? A henley? Or perhap a dress shirt?

Long sleeves, at least two pockets which can be fastened, synthetic fabric, fairly loose fitting (to allow layers underneath), probably light blue in color (not critical)

Never really needed a spare shirt.

Most of onsite work (software developer) was commuting to London, so just bought a new clothing if had to stay longer than expected.

Did like the idea of vacuum packing a set of the essentials (socks, boxers & tshirt) and leaving it in a bag just in case.

Currently it’s a dress shirt purchased from my employer’s corporate logo store. I have three basic work uniforms depending on the occasion (jeans and a collared shirt; slacks and a collared shirt; slacks, sportcoat, and dress shirt being most common). The corporate logo dress shirt will serve for any of these purposes. It wouldn’t look great with a tie, but I think the last time I wore a tie at work was in early noughties.

For the past year my work uniform has been to stash a polo in my home office for any video calls where a t-shirt is inappropriate, but I’ll be heading out to see customers in person again soon enough.

Having a bug out LOCATION is a must, imo!

Whether a person has another piece of property, or a friend’s/relative’s place with a pre-arranged agreement to use it as a BOL, it needs to be organized well in advance of ever needing it!