I lived on Whyte Ave in Edmonton for years. So I was pretty used to going for a stroll up to the Uni and passing tons of bums. Best strategy is to just look forward and say nothing. Ignore their existence. This was when I started smoking Menthols too. I'd get as many bums asking for smokes as I did change. While smoking menthols I had the benefit of putting on a nice guy show by offering, but not even the bums would take my menthols...
For the most part if you just keep walking and say nothing, or just give them a quick no, they aren't gonna bother with you. These bums deal in numbers, and for the most part aren't gonna bother following you down.
I remembr once this streetkid came stolling up to me and asked for a smoke, I said no. SO he raised his skateboard up at me like he was gonna stroke me with it. I straight kicked him right in the fucking gut and folded him on the spot, then rolled his fucking board out into traffic. Not sure what picture that paints of me, but I don't care. I still look back on that moment with fondness...
I'm pretty understanding with most homeless people. We have a guy in town where I live now who lives in an old truck camper someone left for him up on the side of town. he collects recycle and whatnot around town t feed himself. So my roommate and I offered him to come pick up our recycle if he wanted to.
One night we leave a cooler full of beers on the deck, and wake up the next morning to this bum and his buddy sitting on our deck drinking our beer. He said he "thought we left it for him". GTFO. bum ain't picking up our recycle anymore...