One issue with Jayhawks' idea is limitations of the current resupply system.
This is an area that I think needs attention, how can the resupply lines work better. For example the roads/rail-lines/and barge paths, are limited by the 10 minute resupply time. no matter how long you make the route the vehicle will travel fast enough to get to the base in 10 minutes. So if you make the train route long enough, you can have trains going 300 mph, this really limits what you can do with them. I think the vehicles should have an upper speed limit that's historically correct, and allow for multiple trains on the path at the same time. Then give the terrain editor a time limit first resupply vehicle, so it must arrive within 30 minutes (after the initial 30 minute delay, a train/barge/truck would arrive every 10 minutes).
So here are some example speeds,
Trucks- limited to 25 mph, and a range of 12.5 miles
Trains- limited to 35 mph, and a range of 17.5 miles
Barges- limited to 15 mph, and a range of 7.5 miles (yes I know this speed is a bit high historically, but it needs to balance the max resupply time of 30 minutes)
So these are longer routes at realistic speeds and it would only delay resupply in the first 30 minutes that an arena is loaded. After the initial 30 minutes, the resupply would arrive every 10 minutes like it does now.
I suspect this would take some major changes, and may not be feasible with the current resupply system, but it's a step to making the strats and resupply system, better targets.