I don't make it out every day, I do make a 3 mile walk 2-6 times a week. Our weather here in Western WA has been very wet this Winter so I did cut back. Now that the weather is starting to improve we're making it out more often. Each dog is different, he/she will let ya know if it's too far. Sometimes I'll shorten our walk because "I" feel tired.
For a dog that pulls, I highly recommend a harness instead of a collar. Ya want to avoid that collapsed trachea stuff they've discussed here often in the past. Also, at least once, a overly friendly(?) dog approached very quickly, and chased my dogs through my legs and around me... and got my pups worked up so bad I felt the need to hoist my pups into the air and into my arms using the leash and harnesses. I wouldn't have been able to hoist them safely out of potential danger as quickly if they had collars only, but with the harnesses it was a very safe maneuver. I'm sure it looked like hell though.