Very interesting photo! I cannot be sure, but the middle car may be a Knox air-cooled from about 1901 or '02. The T truck is a high-radiator with 30X3.5 front tires so is probably a'24 or '25.
The wheels on the touring car are unusual, rather "deep dish" looking. The hub looks similar to REO at about that time, but I don't know what it is.
Thank you again Jay!
Drive carefully, and enjoy, W2