As a general guide for average conditions, sure, every 5-7 days is reasonable.

For sure it depends on conditions. Yours are probably different than mine. Every 1000+ miles was when I was racing jrs and riding lots of miles, and yeah, it was on clean roads with no rain. If I got rained on, the chain would get wiped and lubed. Rain and wet conditions will necessitate immediate re-lubrication. FWIW I do recall riding one ~2000 mile tour without lubing at all.

Anyhow, the "wait till it squeaks" suggestion was just to make a point. I was a mechanic for quite a few years, and saw many, many more drivetrains destroyed by too much oil than by too little.

OT: FWIW the latest scientific studies seem to indicate that the best time to drink in hot weather is when you are thirsty. The common advice of the last 30+ years: if you wait till you are thirsty it is too late, is now thought to be false.