Why do you prefer 3-5 OF at any outfield position instead of requiring outfielder specific positions? Vice versa?

Personally because it is easier. I just want to draft OF and not have to worry about position. Not sure it is a good reason but it is what I am going with.

I prefer having more OF spots than going with specific positions. 5 OF is better than using LF/CF/RF only for me. If it's a shallow league, I could see trying the three spots to try and add an extra element.

I have never played in a 4 or 5 outfielder league.

I do like LF-CF-RF

If you play in a league where they use LF/CF/RF, you might have to pass on a better player or a player you're more interested in to fill a need. Not always something I like to do, but I do play in a league like that. However, we have 2 additinal OF spots.

We swapped to the LF, CF, RF format last year, and there were no complaints. We also had one OF slot as well as Util, so you could play up to 5 outfielders if you chose. Using the individual positions just requires a bit more strategic thinking, especially at the draft table. Going into last year's auction draft, LF was kinda shallow, but since I had Braun as a keeper, I was able to start a few bidding wars for the few remaining top tier LFs. Good times.

My deep keeper league has LF/CF/RF and plus two more open OF spots. It creates interesting draft strategies. You no longer target based on just OF but by the positions themselves. Can add an element of challenge in deeper settings, maybe doesn't have a huge effect on a standard league setting.