This comes to the YMMV aspect- where you are doing an overnight in your own yard, nice and legal, I'm doing it OUT of town- but a large part of the differences between the two could be as simple as the size of the towns involved. What I'm planning on doing, I could never accomplish if I lived in Manhattan. In a city of 25,000, however, it becomes a much more attainable goal.
If my city were accessible from ALL sides, this would be a pretty good exercise in seeing how long it would take to bug out of it on foot, as I'm smack dab in the middle of it right now. However, the city is bordered by a large creek to the south, and a major river to the east, leaving north and west as the most viable directions. North gets complicated- the next township borders ours with so little change between them, it is literally a matter of crossing a street to find you have changed towns. It's also mostly a retail oriented town, where the main road is just one mall after another, similar to Rt 17 in northern NJ, for anyone who's ever driven "The Gauntlet" there. Speed limits are posted at 30MPH, and no one is doing less than 50...four lanes wide in each direction. It's not for the faint of heart, or new drivers. To the west, there are still highways, but less stores, and the main highway heads into the mountains, with room to walk the shoulder without being hit. I'll be using part of that, most likely. My route will take me west, and then north, curving around our local version of "The Gauntlet", letting me avoid the traffic, intersections, and the recipe for disaster those create in a real disaster. Once north of the city, I can stick to secondary roads, cross country for some of it, or follow a watercourse, to avoid detection and problems. I'm going to be trying to Grey Man my way out of town- between my appearance, and whatever "crises" are sent to me, we'll see how I make out.
Once out of town, I'll have two water crossings to make, minimum. Any bridge could be "gone" at any time, so I can't be lazy about getting to them, and across, or I'm liable to have a text message telling me it just went bye-bye. The second crossing can be waded, but the first means a dip, and I'm not sure how early-morning it might end up being. It's not the water temp or the swimming I'm concerned with- it's with how cool it might be AFTER I get soaking wet. My friends are a bunch of evil, spiteful pricks that way.
I have a digital camera that does stills, video, and also records audio only. I'll be taking that, and spare batteries, with me, to 'record' my bugout, and to read the texts out loud into, so I'll have my record of the trip, and still be able to keep moving. My original plan was to write the stuff down in a notebook, but that means stopping, and stopping means becoming noticed. Plus, where I live, seeing someone with a pack on, walking along a highway mumbling to themselves, well- it's not really that uncommon a sight...
I'll fit right in.
Another issue with the water crossing at the edge of town, which may interest some, is the group of homeless people living under that particular bridge. If I have to swim for it, I may well have to come into contact with them- I'm formulating alternative crossing points to avoid that. I'm not taking much with me, but it would be like gold to them, who have even less. There are two bridges crossing that particular water course, both at the edge of town (the creek makes up the border), and both have a population of homeless people living under them, so A or B, my decisions will likely be interchangeable between the two. Get across, avoid detection. To make the after-action report interesting, I may try to do this close enough to take a pic or 2, and still avoid being seen.
Most of this is going to be roadside hiking, really, and other than the text message 'disasters', probably not that interesting. Roadside may not seem all that grey man at first, but keep in mind that this is an area where there are a good number of hikers and hitchhikers, so even with the pack on, I won't really be that out of place in appearance. Where I may be forced to hoof it overland, I am hoping I'm not going to end up inadvertently trespassing- no matter where, someone owns the property, but some are more lenient about it than others. I always try to be respectful about it, and cross as little as possible of someone's land, and never do any damage to it- this means skirt the sides, in most cases, as there are a lot of crop fields around, and no cutting firewood, etc.