Right on dude! you've got the right idea and I think you'll do just fine. As for sleeping areas, get creative. You can pick a spot that's out of site, in the bushes or anywhere clever. You'll want to constantly keep an eye out for places to sleep as you're walking. You may pass the best spot and come back to it. If you're looking for a spot to sleep when it's dark, it may be more difficult. You can find yourself a spot, make your bed, make a hideaway for your pack and stuff (cover it with foliage so nobody can see it even if they're at your spot). Bars are good for free water, wifi, and charge electric devices, plus if they're nice enough to let you do all of that, then there's probably somebody there cool enough to kick it and share stories, tell you about the area, point out places to sleep.
You'll want to consider rain. Tarps work great and they're cheap and easy to repair with duct tape. If you get a big tarp, you can use it to sleep many people (12'*18' can sleep 4). Green and brown tarps are good because they're kinda camouflage. With a tarp, you can make a tent by just using tent stakes, a piece of string, and either a stick or a tree or fence post or whatever. With a big tarp, you can make an over/under tent or it makes a comfy sleeping mat, but is heavier. If it's just you and not much gear, you could get by with a smaller tarp and some tent stakes and string (this you can set up as an A-frame over [not under] tent). You can experiment with this. I've even heard of lightweight, packable tarps, or shower curtains, but I've only really experimented with tarps. You can search tarp tent on google images and you'll see all sorts of setups that you can mimic.
It can be easier to find a place to sleep in a small town than in a big city. every place has it's own drawbacks though. So get creative with it and you'll learn what you like to do. Don't be afraid of bug bites, but don't ignore them either. the bushes can be great to sleep in, but there is bugs. Stay covered, wool boot socks, pants, sleeves, mittens, scarf, hat, hoody, will protect you against unwanted bug bites. Last year, somebody donated me a bug net to wear on my head. I haven't used it yet because I'm used to bugs, but I may use it if I have to sleep in a place where bugs are eating me alive.