Google tries to get security right for Chromebooks. A read-only portion of the firmware authenticates the read-write firmware. The read-write firmware must be signed by google. You must disassemble the machine to flash the read-only firmware.

The burley trailers can carry 100 pounds (others can carry more), I suspect good enough for your recent trip. If you dont have hills to contend with, it's surprisingly easy to carry the extra weight. Other than slower acceleration (hint: down shift before stopping) you'll hardly notice pulling the trailer. You may get there and back faster than in a car given typical weekend traffic in suburban shopping areas.

You can avoid carrying a lot by drinking water out of the tap at home rather that buying bottled beverages.

If you choose to you can make your life work with much lower dependence on a car. Most people choose not to or are convinced it's not worth trying.