ok, I think the first one was transportation, that's easy - go with the low maintance of walking this way you have one less thing to deal with/worry about.
Sleeping ??
I agree with the person who said avoid backyards.
I went to take a piss inside a new construction apartment [in Brooklyn NY] a number of years back- and had some large objects sent my way, which thankfully none of them connected with me or else I'd be dead.
I also once took a leak [these were nightime pisses after drinking...] in a doorway to a walk up apt and got swung at by an angry man with a bumper jack !!
Like an old school 48 inch bumper jack... again, thank god he missed.
If I were you, I'd sleep on the outskirts of any place I'd be visiting - after carefully checking things out during the day.
Out here where I am at today, there's a dude who sleeps in a tarp wrapped like a blanket around a sausage hung like a hammok out here, I still got no idea how he does it, but I totally avoid that area when out with my dog - and speaking of dogs, my dad told me that his biggest fear [as a NYC Fireman during the 1960s and 70s] when getting on top of a roof during a bad fire was not the fire itself but coming across and irate German Shephard as back then, folks kept dogs on the roofs for protection.
There's also plenty of people camping along the river out here, some for quite sometime, even years.
Out of sight, out of mind I guess you could say.
One guy had an incredible base camp set up high on a rock where he stayed at for close to two years. then he simply vanished without a trace.
Some say he went further north, I don't know but I watched his canoe for him until that vanished too.
His trick was he made it look like he really owned the place, he was an older [mid 50s?] man who always looked clean. so he attracted very little attention.
Weapons ??
Best one - easier said than done - is to simply avoid confrontation in the first place, which I know - that's very difficult to do - if not impossible.
I once pulled a speargun [I'm a free-diver] on someone I decided I did not want sizing me up, I never seen anyone run so fast.
On the other hand, I recently had it gently explained to me that at a particular boat ramp, my safety could not be gaurateed - so needless to say - I don't launch out of there anymore because I have a dog waiting for me to come home.
Believe me, it sucks when one has to compromise one's life out of fear.....
As for wildlife, I have never had any problems with wildlife - even what is called nusence wildlife - perhaps because the animals view me as another kind of animal, I don't know... but I have always co-existed with the animals fine when outdoors.
I could be wrong - but it is probably safe to say that almost everywhere, there are people living on the fringes of society.
They say there is strength in numbers, perhaps your best bet is to check things out and see if there is a group that will let you stay with them or close by.
I myself on the other hand prefer to be alone.
Ralph Nader once stated that as a citizen, we the people own all the public lands.
To me, that means we should be allowed to camp on them.
[^^just some food for thought]
I'm sorry I have no real solid advice for you................ except to go with your gut instinct.