I happen to be living in my van right now, and have done so for many years, and I think there are some factors you have not considered on the urban boondocking thing.
1. It sucks. You are breaking the law in most places.
2. Trying to sleep inside with cars going by constantly, or even sporadically significantly reduces the quality of sleep.
3. You are always expecting 'The Knock' of either law enforcement, or an angry homeowner telling you to move on, or a criminal with sinister motives.
4. Unlevel parking. It affects ease of movement and quality of sleep
5. Constantly searching for a new spot, and trying to remain stealthy once there. Not moving around inside so that street lights, or your antenna do not reflect light, and wobble and give you away.
6. Remaining silent. Phone calls? Forget it.
7. Bathroom activities. The best and biggest Pee bottle still needs to be dumped, and the smell can knock you out in an enclosed space. I've never used a porta potty, but do not imagine emptying one is fun or convenient. Using public facilities is a last but necessary resort at times.
8. Climate control. An exhaust fan on the roof reduces the stealth factor, and fresh air has to be allowed to enter somewhere for there to be any recirculation. This equates to more noise transferring inside and out, and less security. In the winter, you sleep under a ton of blankets fully clothed, or keep your clothes under the sheets with you. The inside air gets very stale, and you can wake up with a headache.
9. Vanxiety. Even with all your stuff locked up, and hidden, whenever you are away from your home, there is the worry factor. I constantly have nightmares that I can't find my Van, or that it has been broken into, or I'm watching tattooed gang members driving it away while drinking my beer and laughing.
10. 'Down by the river' Jokes. People and friends might say they admire your lifestyle and freedom, but you become the guy who lives in his van. It is how people will refer to you. It does not matter if you have twice the intelligence, and prospects as someone else. The stigma of being the Guy who lives in his Van, will lead to bitterness, anger, self imposed isolation, and a general hatred of humanity, despite awareness of it and attempts to mitigate it.
11. Give up any prospects of a meaningful relationship with a woman. She could never impress her friends with you, will never think about staying with you while burbdocking. If you do find one granola enough to accept your lifestyle, can you accept hers?
The only reason I still live like this is because I have a level parking spot on private property in a safe neighborhood. I have access to my own shower and bathroom, and this negates most of the inconveniences of this lifestyle.
But there is still the social stigma, and Vanxiety when parking elsewhere.
If you are to remain in any one area, I urge you to seek a private secure parking spot. It makes a Huge difference. If You are just passing through an area, then it is easier to get away with this lifestyle, but you are still considered an undesirable, no matter your motives and education.