It sounds like you live/travel in relatively safe places and as such even a 5 round revolver is more than likely adequate.
I am out at past midnight at times on foot, sometimes driving through known murder capitals heading into a warehouse/industrial park when hardly anyone is around, etc. Personally, I feel if I do have to ever pull a gun out on someone; it's going to be 2 or more people.
I have been fortunate enough that words and some OC spray have been enough...also more than likely having my dog with me some of the time.
Too many think it's easy to hit someone on the street...so often you are trying to move, they are definitely moving and you have uneven territory with obstacles. Even seasoned pros have a much lower accuracy in the field than at the range.
No one is hoping for a shootout, most of the time on first shot the asshats are going to run away. However; we have all read about those that don't give up and have some dude pinned down and he couldn't get away.