Yeah, preferences and habits change. The mind gets used to doing things a certain way, I guess.
In my case, I walk barefoot as much as possible. Have done that already before I ever meditated. In that sense, it's not new for me.
Sometimes, due to pain, I do have to wear shoes during walking meditation, and sticks to support the posture. Something I got used to as well after a while.
For me the sitting posture was more challenging. I'm not even able to do full lotus. Even so, it really was difficult and painful. Now, most of the time when I sit down, the body immediately relaxes and so does the mind. Same happens when I pay attention to the breath during daily life thingies.
Next to that, I've never been much of a social butterfly, but nowadays I find myself in silence and separation more and more. All sorts of things have changed due to meditation.
So, my answer is yes. I have the same experience as you when we are talking about something new being uncomfortable to begin with and comfortable after the 'getting-used-to-period'.
It's sort of encouraging, isn't it? Tells me that the mind really can do a lot, change a lot. :)
Not sure that this answers your question though.