Congratulations! My Sims always purchase tickets, but I've only ever seen, like you, Townies/NPCs win. However, I should mention my Sims are all very well-off, too, so for them it's more like giving to charity, if you will.
I would have him keep his job and give him the frugal Trait so he can invest his money to continue to grow it. You never know when he might need a larger house.
As for the neighbor popping by on a whim? News sure travels fast. I wouldn't trust her, either. LOL (Does make me wonder if some long 'lost' cousins will make their way over to your Sims place, too. Now, that would be some fun gameplay.