Upvote:2
Based upon what you wrote, you are building up a history of performance and this will work in your favour. More so as time goes on...
While our laws theoretically allow you to apply for visitor visas back-to-back, they added a new rule two years ago that prohibits building up a life in the UK by frequent/successive visits, and so if they think that you are attempting to build up a life in the UK, you will be vulnerable to a refusal. The wording and interpretation of the rule is purposefully vague.
For your question: "Is it easier"? The answer is that it does not matter. It is a dreadful mistake to assume too much in a UK visa application regardless of your history. Each application should start from first principles and assume that there is no preceding history. Plan for the full 90 days processing time. When your history (along with application quality) satisfies the ECO, he will automatically get back to you and ask if you prefer a visa with longer tenure, like a 2 year etc. It is his decision and there is nothing you can do to promote it or persuade him.