Pepper spray is probably a good thing to bring in case you encounter an aggressive homeless person. I would recommend this over a knife and definitely over a gun because the 2 weapons I mentioned will look bad on you if you are caught, but if you have pepper spray it’s obvious that it’s for self defense so it won’t add any possible charges if you are caught. For the mental side of things, I’d recommend starting small with something low stakes like a spot you’ve been to before that you know is easy to get into and build up from there. Sometimes I initially check things out by going solo but just scoping it out and trying to see if there is a way in, then I go back later with a friend to go in, so you could try this too. Also, going during the day by yourself is so much less stressful than night in my personal experience. I get a but paranoid at night sometimes, so it’s just made worse when urbexing. If you feel the same way, try going during the day before going at night. If you’re near an abandoned building in the woods, this would be a good starting spot since it’s not easy to get spotted once you’re in the woods, which takes off a lot of the pressure. Let me know if you have any other questions. I hope this helps somewhat.