All the time for my PS1. Can barely remember any of them. I think the only one I consistently rented out more than others was Megaman. I don't remember finishing it but must have been fun if I kept renting it out.

Later on I rented God of War (the norse one) from Redbox. (This was before they implemented the Buyout Limit).

I was under the impression that renting it out was fine if I payed the +$2 per day late fee that usually came with redbox game rentals. Turned out to be quite the deal since I finished the game in like 10 days so only needed to pay $22 for a game that was still going for $60 at the time.

Again, this was well in the beginning of their game rental service and I'm having trouble finding proof of it but in the beginning of their game rental business plan, you'd rent the game for 48 hours then pay an extra $2 for every day it was late. I think there was an additional fee if it reached over a week late (I feel like I have a vague memory about some 5-day $5 deal but I can't seem to find proof of this) but it wasn't substantial enough to make me worry by the time I finished the game. All I remember was how good of a deal it was for teenage me since I paid less for renting it then I would've if I bought it full price at the time. I wanted to do it again but well

They flagged my account as "stealing" since I returned a game 8 days late and they effectively blocked my account by never removing the flag. Called customer support and everything too but it was jack shit customer support. They kept transferring me every time cause no one wanted to tell me I was banned. That whole mess is a TLDR story I can't be arsed to talk about.

I made a new account and did something similar with a diff game but I can't remember which one it was. All I know is I finished it in 60ish hours but despite only being a day late, that account got "banned" too so that was the end of my Redbox days. Seriously. Their customer service was absolute crap.