Went to the website and read the idea, sounds great, almost like hydroponic systems. Don't even ask where I learned about those. Weed control would be a snap, if you even had to worry about it at all. The tomato plants could be sheltered during the winter and regrowen next year with the established root system.
Absolutely. I've built two...one with tomatoes, and one with a small herb garden...basil, thyme, chives, etc. They're kind of heavy, but are transportable. Insects are easy to control in them. Keeping the damn cats out is another story, lol!
There is a DIY site called instructibles. There are several sets of instructions for container gardening. Here are several similar to josh's.
https://www.instructables.com/id/Another-ez-cheap-Earthbox-clone-without-PVC!/
https://www.instructables.com/id/how_to_make_an_earth_box/https://www.instructables.com/id/Earth-Box-from-a-Plastic-Barrel/
Once you are on the site, just do a search for "container gardening" or "earth box." There are a LOT of things there from woodworking to whatever.
John