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Call me crazy but the title itself reminds me of Goldilocks and the Three Bears.

This calls to question what is meant by comfort. If comfort is the lack of suffering then I'd say that's precisely what Buddha wants for us.

I think the Middle Way is comfortable but not too comfortable. We have to adapt to change.

When I think of self and the Middle Way, I always also think of the Two Truths. When we talk of these separate selves as an illusion, it isn't that they don't exist but that they are misrepresented by the senses. Like the rope we thought was a snake for a second there doesn't disappear with the snake. The illusion is dispelled but reality keeps on.

I think these separate selves are illusory tools. When we see through the illusion, we don't throw away the self, we keep on using them. Buddha kept using his as a tool to teach others. He almost didn't though. If it wasn't for Sujata showing him compassion and feeding him rice, he wouldn't have.

Is the practice to increase the frequency of "tranquil days" or to transcend the beings experience so tempest or tranquil come and go all the same? A marriage, a divorce, a birth, a death, the body responds, the thoughts respond, the feelings respond, but there is no being there? The tears still flow, the smile still forms but there is no being there to push it this way or that which makes new karma? Is this how past karma is worked off and future karma is not made?

I wouldn't say there is no being there but that we are calm. Being fully here now is the idea, not being carried away.

Karma is the causation of action.

As I understand it, in most traditions comfort is seen as not important for the serious practitioner. Look at the emphasis on correct posture in zazen, and the often-repeated instruction to ignore minor discomforts. I’ve known people who have done themselves significant damage (permanent numbness) by pinching nerves in meditation and ignoring the attendant warning signs.

Most meditation centers therefore supply chairs and cushions and don’t insist on posture but instead have taken an accommodating approach. Its much friendlier to beginners, and it means there is less chance of getting sued!

Ultimately there is a middle way to be found here as well. If you focus too much on comfort, you disturb the stillness of the body on which meditation relies, if you do it too little you could do yourself an injury.

While the Buddha did not seek comfort, was the middle way comfortable?

I would say it is more along the lines of 'satisfying/fulfilling

Is the practice to increase the frequency of "tranquil days" or to transcend the beings experience so tempest or tranquil come and go all the same?

I guess the answer to the above is all of the above...To develop a sense of inner peace...

From what I gather, the subtle sense of self remains as a tool ( so one can interact with the conventional world) but the clinging aggregates are now Teflon coated so to speak...where Awareness no longer fuses/adheres to the clinging aggregates experience...In other words the more solid sense of self the "I" AKA the Ego no longer plays a dominant role in the phenomena arising/the drama unfolding ...

"May I clearly perceive all experiences to be as insubstantial as the dream fabric of the night and instantly awaken to perceive the pure wisdom display in the arising of every phenomenon."
~Part of a Tibetan Buddhist dedication prayer~

If you think about our habitual patterns, how we react in certain situations and not so much act.... And it's when we become more 'aware' (from which I gather practicing the middle way develops this awareness) of these patterns the less likely we are to follow through/react....

So I guess one could say the middle way leads to a tranquil way of life... Gradually changing those Dukkha moments into Sukha moments ( Sukha as in, where Dukkha no longer causes disturbances)

We are just vibrating bundles of energy flux held together by karmic glue, automatically reacting to situations, until the Dharma starts to flow on through...

I guess in the long run @FleaMarket we have to see for ourselves "Ehipassiko" AKA "Experiential Understanding"...Words can help to describe an experience but they are not the actual experience....

It pays not to let the mind become charmed by its own thoughts...

There are as many forms of meditation as there are forms of love. Some focus on comfort. The Buddha paid little attention to the seeking of comfort or discomfort and called his particular practice between them, "the middle way".

I think there is an important distinction to be clarified in** Buddhist** sitting meditation between searching for comfort and being able to accept where you presently are, whether that is comfortable or not. Most folks who get involved with meditation in order to find comfort, and who never transcend beyond that motivation, end up falling away from such a practice when faced with the physical, emotional, and mental challenges that inevitably disrupt that comfort.
Birth, old age, disease, and death are not comfortable and will be everyone's past, present & future experiences.

Yes, it's good to choose a posture that allows you to remain alert as opposed to sleepy, and grounded as opposed to unnecessarily distracted, but the Buddha's path towards suffering's cessation is about the simple and direct unraveling of all of our attachments, whether they are comfort supplying or not.

Over the years my sitting has changed. How about you?

At the moment I am sitting without a cushion. Chanting very quietly. And modifying/relaxing any posture stiffness, The relaxation is part of how I am doing the Medicine Buddha chanting/focus. So the mudra/hand position goes through some interesting convolutions/softening.

I am starting to use the half lotus again but am in no rush to return to full lotus, kneeling or corpse meditation (yoga nidra).

For me there are some important reminders:

-medition is mostly attentive awareness
-'Bad' meditation is still pretty good
-find comfortable, not more suffering

... be interested in others insights/changes/preferences ...

Am I too broad in my new ageyness?
https://www.mindbodygreen.com/articles/the-12-major-types-of-meditation-explained-simply