The guy knows what he's talking about.
It applies to any level of homelessness, not just urban.
If you maintain yourself, and you look clean and safe, you'll have an easy time convincing people that you're adventurous rather than destitute. Adventurous gets you much farther than destitute, because secretly (or not so secretly) a lot of people our age want exactly what you have--The freedom of the road, no responsibility, time to write and reflect, no obligations, nothing but days and weeks to focus on yourself. Being destitute might get you a dollar or a cup of coffee. Being adventurous might get you in a pretty girl's bed, or better yet, a hot shower..
No kidding. Mixed with his previous section on proper hygiene, this really works. In my hobo days, I did the Mick Dundee thing (this was during the time that the Dundee movies were out and everyone was going Australia crazy). Have a canvas pack, cargo pants and shirts from Panama Jacks (back when they actually sold outdoor gear) a boonie hat and a passable Australian accent got me pretty far. One of the major things was keeping clean. Not just for health reasons, but like the quote above, it makes you an adventurer, not a bum. Doing a bit of legwork on three or four locations in Australia, I had enough to BS the average American into buying the "Aussie on a walkabout" schtick.
I often got asked why I would come to the US to do a walkabout when I lived in a place as exotic as Australia. I'd tell them to keep in mind that to an Australian, the US is the exotic country, plus, I could find all kinds of terrain and just about every climate within its confines. Add a bit of flattery to the American Sheilas if I was talking to a woman and they ate it right up. I could almost always bum a ride, and often get offered more just for telling them BS stories of my travels. This will not work if you're in the guise of "filthy bum".
One exception to the linked info that I made was to use cologne. Not much, just get a small bottle, put my index finger over the opening, slosh it once, and then draw a line down my chest (use the back of your neck for short guys). It's not enough to smell across the room. But makes it like you're obviously not covering stink, and care enough about yourself that you probably have some class.
Another tip they hit on is buying a gym membership. Without house and car payments, it's not hard to save up quite a bit of dough doing temp jobs and the like. Buy a year membership at a nationwide gym. I went with Gold's. Yes, you get to work out and exercise. But you also (usually) have access to a locker that you can stash your stuff in for a day, and a shower. If you go in non-peak times, you can also do a quick clothes washing in the shower.
Other tips:
For showers, you can also use truck stops, churches often will have a shower for precisely the poor like you. Shelters will usually let people who don't live there shower at certain times of day, and usually allow you to do one load of clothes once or twice a week. Sometimes they, and churches, will have toiletries to give away.
Churches are a great resource, even if you don't believe and I didn't at the time). Pick a small church. when you go in,
don't ask for money. Ask for what you need "Hey, guys, I'm down on my luck, I need some help getting some food and maybe a shower, or a load of clothes done." Now,
before they answer, bring up that you hate to mooch (even if you don't), and you notice that they have leaves on their lawn, or the carpets aren't that clean, and offer to rake the lawn and bag the leaves or vacuum the carpet, or do some kind of work to "buy" what you need. This usually goes over real well. They are also far more willing to help someone that takes care of themselves and isn't drunk or on drugs.
They'll probably invite you to services. Go. Why not? You get to enjoy A/C in the summer or heat in the winter for a couple of hours, get people to talk to (very important when you're on the bum), it's a
great place to network to find jobs, places to live, etc, and who knows, you might get something more out of it.
You may think I'm a bastard for recommending that, but there's nothing bad about it if you are really needy. Believe it or not, they
want to help people, especially those that aren't lazy and really do want to help themselves, and aren't just there looking to mooch free food and money for dope. Again that clean appearance comes into play.
Final tip for this post: maintain a current driver's license. Having a current license, and hopefully some money (at least a 20 and some singles), plus being clean and not having dope or a bottle of booze on you will get you MILES when dealing with the po-po or anyone in authority. If you can get them to buy the "walkabout" story over the "boozed out bum" story, they'll often help you, rather than hinder you. Or at the very least not roust you (unless you are crashing out in a nice neighborhood, then you'll get rousted, every time).