Joe, working with thin magnet wire can drive one crazy - "burning off" the enamel coating and soldering to tiny-fragile surface-mount-device (SMD) LED terminals.
Did you consider using pre-wired SMD LEDs sold at eBay (and elsewhere)? Hundreds of choices on eBay but not sure if the size, style, wire-diameters, lengths, etc. would be compatible with your specific poles. But they seem reasonably priced at, say, 50 cents a piece.
As for how to wire up (distribute) power to dozens of wire-pairs with lamp post LEDs, the often discussed eBay vendor "we_honest" has a reasonably priced board designed for this specific purpose.