Love the project and I look forward to following this from a readers perspective after spending an entire year doing exactly this same thing. I will start out with three pieces of advice:
1 - The Model A is a wonderfully simple and rugged vehicle. If you take care of it, it will take care of you.
2 - When it comes to breaking down (and you will) be very careful not to over-diagnose. Always eliminate the simple and easy possibilities first. I have plenty of stories where I thought the worst and it ended up being quite simple. I even towed it once suspecting a head gasket to later find out a five-minute roadside repair would of have fixed the real problem.
3 - Keep a handful of spare parts with you...mainly a full gasket set, and extra ignition parts (especially spare points and condensors). With a basic tool kit and these items you can take care of most side of the road annoyances.
Lastly...I noticed you were pulling the car on the trailer by the front bumper. I found out the hard way that if you use the bumper to do this you will eventually break the front mounts. Use the front axle instead...
Have fun and let me know if you have any questions!