I always thought these would be best for transporting cabinets. With the EZ load ramp you could load it alone if you had a dolly, and would minimize risk of damaging the games. I don't think they cost much more to rent then a truck, if you were planning on renting a truck anyway this would be the way to go.
I used an old CRT TV with my Pi 1 B+. I used the video/audio out, not the HDMI. I used a GP Wiz40 for my joystick and buttons (note that you will need 2 if you want 2 players with 8 buttons each). I'm not quite done with it but it's functional. It works well, I think this is close to what you're trying to accomplish.
It feels very retro and the sound is great. I moved the speakers out of the TV and put them right at the bottom of the bezel.
Note that if you use Retropie the menu is made for HD, so it is difficult to read the text, but possible. There is yet to be a low def theme available that I know of.