On the topic of FD getting from Lapham Road to JD's house on Welles Lane, as a local I'll try to give the group some perspective.
If I had to leave a car on Lapham and get to Welles Lane myself and didn't want anyone involved I'd consider 1) Train from Talmadge Hill to NC Train Station then a Taxi paid in Cash from NCTS to either the bottom of the cul de sac at Welles or to the Winter Club on the corner of Ponus Ridge and Frogtown (quick walk/jog from there to the house); 2) Jog from Lapham via Old Stamford Road to NC Train to Taxi; 3) Jog through Waveny to South Avenue up to Farm Rd to Old Stamford to NC Train to Taxi; 4) Uber/Lyft readily available in NC, with burner phone/Prepaid card.
If he jogged or walked from Lapham Road at that time of day on a Friday when school was in session, there are people driving to Talmadge Hill Train Station for trains to NYC, there are school drop offs at NC High School, Saxe Middle School and East Elementary School very close to Lapham Road and plenty of joggers so tons of people and activity to blend in but the route to her house is very dangerous, particularly in either getting to Ponus Ridge and approaching Wells from the safer direction on Frogtown or getting to Welles on Frogtown from the much more dangerous Weed Street approach. And besides the Country School, West Elementary is just North on Ponus Ridge so again, lots of traffic but people do jog all over town.
As far as a run to JD's house on Welles from Lapham Road, (in case you want to follow via Google maps):
A. The most direct way to run would be to go North to 106 Old Stamford Road up to Richmond Hill Road (has a train crossing that stops traffic and walkers periodically) to Weed Street, quick Right and left on Frogtown. Pretty safe until Frogtown which is super dangerous from that point on to Welles.
B. Crossing at Jelliff Mill from Old Stamford to Ponus Ridge is pretty dangerous but fairly straight with yards to jump into if a car comes flying at you and then is definitely not too bad after that. So that would be Lapham Rd to Old Stamford left to Jelliff Mill, right on Jelliff Mill , Right on Ponus Ridge, Right on Frogtown.
C. The other practical option is same as A but instead of a left on Frogtown stay North until Irwin Park and cross over to Ponus Ridge on Wahackme. If my kids had to do this walk/run, this is the route I'd send them. Then go left on Ponus Ridge, left on Frogtown to Welles.
Hope this isn't too detailed to be of some use.