I am (possibly too much so) very practical when it comes to making decisions about my home and all I can think when I hear skylight is leaks, condensation and dirty glass. The room looks to have a door with side lights and a sizeable window? Is it dark feeling to you? Just wondering what is pushing towards one?

I love skylights- properly installed they never leak (I have had them in my last two houses)

There are practical concerns though. Could this location let in too much light or cause glare? How far is the roof from the ceiling and how will that transition be handled? What about the wood cladding, can it be matched?

@hallett Those are the questions I’m looking for ideas on. The roof will be say 3-4 feet from the ceiling.

Any ideas on how to do the transition from ceiling to roof?

Anyone have design ideas on what to do with the existing wood tray?

What direction does it face? I'm in the south so always face my skylights north if possible though in my last house we had a west facing one on a staircase (yes hot late afternoon but the transformation was worth it)

How is your attic constructed, traditional or truss? What is your insulation- fiberglass on the ceiling or foam up under the roof deck?

What is the wood ceiling made from? Can you match it?

What side of the house does that exterior wall face -- is it a dark north side?

Another idea you might consider to add light is to add a gable with windows to the roof above the room IF the dormer would face the amount of natural light you are wanting to add to the room.

https://www.pinterest.com/pin/360639882636859064/

This side of the house faces south, so it’s weird that the room feels so dark. I think the roof eaves end up blocking the sunlight. The gable idea is cool tho probably more than we want to do right now.

Other ideas?

How large is your overhang? Skylight or greenhouse roofing in overhang?

https://www.pinterest.com/pin/294352525616539048/

Skylight cupola?

http://domelskylights.com/2014/08/cupola/

H f we can only provide ideas based on the one picture provided. Can you show the outside? Room from other angles? Budget?

A skylight would be installed and then the distance from the ceiling to the roof gets drywalled as you see below.

This is what the outside looks like.

The windows in the center of the pic are about where the skylight would go. If the distance between the ceiling and roof is drywall, what’s the transition between the wood tray & the drywall?

There are some images here that may help: https://images.app.goo.gl/CXEs14ZioN6x2KMu5
I have my doubts about a wood-clad shaft because it will absorb light, but some of these are quite attractive.