Our HOA takes care of all tipping for the garbage collectors (which is handled by the city, we just have big dumpsters no bins), gardeners/landscapers, and the maintenance crew. I think there might be a few others, they send out a letter to all of us who live here in mid November (this year it came a little earlier) letting us know if we'd like to contribute to the annual tip for *List of Services* please stop by the office between X time and X time, by X date. They usually have a card for each place and you just give whatever you'd like and can sign the card. Some people drop off their own card, or some goodies, and they'll take those too (though they ask all goodies be non-perishable). You don't have to tip all services, they do ask if you're giving cash to let them know how much you're giving just so they can keep track of what has come in and make sure the right amounts get to the right places. I find it very efficient. One of the HOA people told me, when I asked, that they already have a set amount they'll tip for the each service for the year, what we give is just extra.
In regards to OP's question, no I wouldn't be sending cash to his home address. That just feels off. And really, anyone could tape a card to your bin. I'd be wondering if it was some random person hoping to score extra tips. I'd feel more secure sending it to the company or handing it to him directly.