We all have different opinions on that. In my opinion, if the tortoise is big enough to self hydrate and is living outside, he is big enough to get his own drinks and I have waterers in the pens that they can climb into on their own. I've seen all of my outside tortoises in their waterers at one time or another.
My Russian is probably 5-6 years old. I will put him in the water dish every day either in his outside enclosure or inside his night enclosure. It's low enough for him to get out of if he wants. I don't make him sit in it. About once a month I will do a soak. I do this for my leopards too, except the one which will soak himself often.
I still soak every other day, even though the humidity has been high and he's probably fine. But he is really hideous about doing it himself! Plus it will give them an opportunity to drink and rehydrate.
I soak mine every other day he/she loves it and I spray her 2 to 3 times a day
I also have a water bowl which he/she uses but mine lives inside not outside cause we live in UK
My tort is a 5" Russian staying outside right now.
All the advice is helpful. It is very humid in summer in OK and he has water dishes but I never see him in them. I think I need to soak him frequently so I know he is getting what he needs. Gave him a soak this morning, then put him back in habitat with breakfast. I think he smiled.
Much thanks!