Personally, I don't care how "safe" people feel coming to my door. The personal protection of my family exceeds any concerns of people coming on to my property. I do live in a somewhat isolated neighborhood on the outskirts of town now, so we don't get those types of beggers anymore, though.
Carrying my firearm around absolutely everywhere I go, I've found that here in Arizona, most people are extremely accustomed to it. I can count the number of times that someone has said something on one hand. The exception to that, of course, is the snow birds that come to area here in Sun City every winter. Some of them can't get used to it. Working in Law Enforcement for the last decade, though, it is never the person who is carrying open that you need to worry about. All of the criminals have their weapons hidden.
For your care packages, Goodwill is an excellent place to pick up some of those things for really cheap. I've picked up blankets, sweaters, pants, unopened toothbrushes, etc. for as little as $1 each. Generally, I pick them up with they are $2 or under. I even found a nice sleeping bag for $3 once. Every other Saturday, the stores have a half-price day where absolutely everything is discounted down. You can put together a really nice package for mere pocket change. Another excellent thing for them is candles. The homeless can use them for a bit of heat, mostly for their hands, but it's a really comforting thing to have for them at night.
