Either way, Strava does the timing........so there's the chore of setting up the segment so that people don't accidentally "false start" the timer or have the segment grab a ton of "weeknight worlds" rides passing by.
I usually try to go pre-ride and create a segment where you have a little 200 yard "dog leg" of some kind off a side street or some feature where there is almost zero chance someone has ridden that segment before outside of a TT.
I think the easiest thing though is see if people would meetup in the other town. In town we have the arena. Almost zero traffic, wide wide lanes. Safer. Good for a beginner.
I think the ideas of different types is a bit ambitious. And perhaps confusing.
Raleigh Brewing is an easy 2 to 3 mile warmup from the arena and the route there you can take is also mostly hidden from traffic.
I did the "Arena hour" segment this year, so I can use that to go in and create as many segment distances as I want. There's already a one lap, and a 21mi segment. I'll create a 10mi, and I'll create one for 25mi......I did do 25mi the day I tried the "Arena hour" as I figured......I've gone this far, why not.