I mean it's up to you, Twitter algorithms change all the time and are hotly debated on whether RT is as good as making an initial tweet, but you also erase all the engagement you made with that intial tweet every time you delete it. Over time, even if a tweet doesn't get likes or retweets, it will gain views--and those views are part of engagement. And, just because a tweet doesn't do well initially in whatever timezone you're in, it may pick up overnight if the right person Retweets it.
But I don't think Retweeting something three times a day is the answer either, so I don't have a hugely retweeted timeline to worry about (and it would be a worry if you had that type of timeline, you're not wrong). I retweet once the next morning and then I just make a new post the next day of something else.