For mishloach manos, matzah rounds, car-menorah parades, and mivtzoim visits, the request is always the same: here are the addresses and the drivers, make the routes short. Plain ChatGPT is the wrong tool for this. Ask it to route two hundred stops and it will refuse, stall, or make something up, because a language model is not a map.
If you can spend a little, purpose-built route apps do this well, and most offer a nonprofit discount. Tools like Circuit, Badger, Spoke, and OptimoRoute take a list of addresses and turn it into an optimized route, usually with a free trial so you can test first.
If you would rather not pay and you can plan ahead, the community wires up free mapping engines with a bit of AI help:
For a turnkey matzah or mishloach manos operation with volunteer assignments and live tracking, some shluchim use a ready-made service rather than building anything.
The tools, prices, and the do-it-yourself recipe are on the community wiki.
Discussions are coming soon. Every skill, app, and guide will carry its own thread where shluchim compare notes on what worked.