Hey Russell,
Good to hear from you! Phew! What a journey!
I suppose the easiest way to clear the basement was to move. 
If you use building flats/fronts along the wall at the top of diagram, you should be able to create some space for trolley. I can also see enough space around the inside edge to have the trolley run from one side to the opposite, perhaps, have a couple of stops in between.
If you want to keep it simple, I would change one of the spurs at 7 o'clock to the opposite direction. The trains would run in opposite directions. I prefer that than looking at two trains racing. Depends on Dad's preferences.
I just went to a redo of my machine and I am still getting things configured. I'll tinker with the plan(s) if you like.
The trolley will be cool. Look at Dallee and Azatrax for some ready to go controllers to make it have starts and stops. Then, create the run. I think from city to country on the inner edge would look the best.
Say Hi to Dad and let him know Moonman was asking.
