I don't know how to attach multiple pics, but here is looking further left...

And still further...

This photo illustrates the extent of the remodel done before us. I am quite certain an architect wasn't hired, nor were any decent contractors. :( between the ceiling jog and the posts....ugh!

Finally, the view from the slider...this is why I want another window on the wall!

Oh...forgot...looking to the right (down the hall...remodeled bedroom would be to the left...not through the door, that is our closet/pantry).

Here is a picture I took of our kitchen a while back...(now you can see the entire front room).

And, just for comparison...the kitchen before we purchased the house (hubby and I are good at visualizing potential!).

Ok, last one! The old dining room...

I understand what you're trying to accomplish, but personally I wouldn't want to give up space in my living area. There are other ways you could layout your LR furniture so that you could enjoy the view thru the slider and it would save you moving the fireplace and adding another window. I see you have a large window on the left wall and if this is a TV watching area I would hesitate adding more windows.
Keep in mind that moving the fireplace would not be a minor expense and I'm not sure adding a jog in the hallway next to the kitchen would be an improvement.

How old is 'kiddo' and how much time does he/she spend in the room? Is it possible to set up the 3rd bedroom as a playroom or study instead of trying to make the BR larger?
If the ceiling is the main annoyance I suggest you change the ceiling. Have a contractor check out why it's built as it is and see if you can't change the ceiling line to a vaulted one.

All bedrooms are in use (2 kids and ourselves). We only have 6 more years w/ kiddo :(, which is why I vacillate.

The ceiling jog is simply due to where they added on and went from stick frame to trusses (the add on). Even the roof line jogs up an inch (sigh). We would have to drop the ceiling to even it out; vaulting the ceiling would be cost prohibitive. Unfortunately even the sheet rock that is currently in place is uneven (varying up to an inch across the ceiling).

Everything else, hubby and I could do ourselves (remove/build walls, move pellet stove, add windows, etc..).

I think I'd leave it too. 9x11 isn't too small. Is there something else you could do IN the room to make it more livable for the kid?

"We were lucky to afford the house we have"....I would search for minor ways to improve the home, including the son's room as kirkhall suggested. It seems what you are considering will cost you considerably, and given your statement above, it also sounds like you are not made of buckets of money. I wonder how you would think about this in 10 years especially since you have done so much already and are able to enjoy such significant improvements.

I worry about what I'll think 10 yrs from now, too. I also know my child won't have all of the toys in another year or two, either.

I wish I could figure out the darned ceiling. I have considered fake beams, soffits, adding sheet rock...ugh. It is just so oddly placed.

That, and the shape of the LR. Long and skinny. I actually don't mind the size too much, just want more windows!

Oh, and the cost isn't too bad...just over $2k (not including new flooring in the bedroom). Remember, we do most everything ourselves.

My kids grew up in bedrooms that are 7x11. My 18 yr old is still in one. I would leave it alone.