If you're not interested in doing and learning how to maintain a bike, you'll be looking at a lot of shop time down the road. Most bike related maintenance is simple and straightforward, especially if you like tinkering and watching Utube videos for guidance. You mention you might like a more upright riding position in time, then I would be looking at the trucker, with the understanding that I'm going to be 'tinkering' on it sooner rather than later. Only you can make that call for yourself, though. Good luck and keep us posted,