Do the recurrent rides get easier the more of them you do?
It helps that we are part 91 so there is really no jeopardy. There may be a way to "fail" a 61.58 but, if there is I can't imagine what it is. There are pros and cons to this. On the plus side, stress is very low so you are free to make mistakes and learn without concern for your job.
On the downside -- well, let's just say that there will always be pilots who lack the professional self discipline to study... especially when they know there is no penalty for failing to do so. Personally, I find it very frustrating to go through training with someone who doesn't put any time or effort into preparation. It's very apparent both in the classroom and the simulator when they don't and, everyone knows, your sim partner can make or break you.
Some people need that jeopardy to encourage them to study. I personally feel like the better pilots are those who strive for excellence without the need for a carrot or stick.
So, to answer your question, some parts of recurrent do get easier over time. The things you do every six months - steep turns, stalls, v1 cuts, circling approaches, etc... those become second nature. More challenging scenarios never get easier... and that's probably a good thing. You want to come out of the simulator a little bit humbled. It's good for ya.